ChemicalBook > CAS DataBase List > [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID

[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID

Product Name: [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID
CAS No.: 227626-60-0
Chemical Name: [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID
Synonyms: BOC-GPN;BOC-GABAPENTIN;Gabapentin N-t-Butyloxycarbonyl;N-rt-Butyloxycarbonyl Gabapentin;BOC-1-AMINOMETHYL-CYCLOHEXANE ACETIC ACID;2-N-BOC-AMINOMETHYL-2-CYCLOHEXYLACETIC ACID;Boc-2-(1-(aMinoMethyl)cyclohexyl)acetic acid;[1-(N-BOC-AMINOMETHYL)-CYCLOHEXYL]-ACETIC ACID;[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID;2-(1-(((tert-Butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid
CBNumber: CB7768192
Molecular Formula: C14H25NO4
Formula Weight: 271.35
MOL File: 227626-60-0.mol

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[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID Property

Melting point:: 127-128 °C
Boiling point:: 422.9±18.0 °C(Predicted)
Density: 1.072±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: Dichloromethane
form: Solid
pka: 4.72±0.10(Predicted)
color: White

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Safety

HazardClass: IRRITANT
HS Code: 29225090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC

Product number: B693565
Product name: N-rt-ButyloxycarbonylGabapentin
Packaging: 50mg
Price: $50
Updated: 2021/12/16

Usbiological

Product number: 005410
Product name: N-rt-Butyloxycarbonyl Gabapentin
Packaging: 250mg
Price: $418
Updated: 2021/12/16

AK Scientific

Product number: 7763AD
Product name: Boc-gabapentin
Packaging: 100mg
Price: $35
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB49884
Product name: Boc-Gabapentin
Packaging: 50mg
Price: $40
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB49884
Product name: Boc-Gabapentin
Packaging: 100mg
Price: $60
Updated: 2021/12/16

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[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

Protected Gabapentin (G117250). Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

Synthesis

24424-99-5

60142-96-3

227626-60-0

Example 39: Synthesis of [1-(tert-butoxycarbonylamino - methyl) - cyclohexyl] - acetic acid; 2-(1-(aminomethyl)cyclohexyl)acetic acid (10.0 g, 58.4 mmol) was dissolved in tetrahydrofuran (280 mL) and 1N sodium hydroxide solution (128.5 mL) was added. The reaction mixture was cooled to 0°C and di-tert-butyl dicarbonate (14.0 g, 1.1 eq.) was added in batches under vigorous stirring. The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. Subsequently, the tetrahydrofuran was removed by evaporation and the aqueous layer was washed with ethyl acetate (3 x 50 mL). The aqueous layer was acidified with potassium dihydrogen phosphate (44 g) and foam generation was observed. Gradually, the foam was replaced by a white precipitate. Stirring of the mixture was continued for 2 hours, during which time potassium dihydrogen phosphate (1 g) was slowly added. The precipitate was collected by filtration and washed with water to afford the target product 2-(1-(((tert-butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid (15.2 g, 96% yield). Mass spectrum (MS): 272.1 (corresponds to C14H25NO4, [M+H]+); Melting point: 181 °C (decomposition); Elemental analysis (C14H25NO4) (calculated values) C: 59.52, H: 9.36, N: 4.76; (measured values) C: 59.51, H: 9.03, N: 4.87. IR spectrum (KBr, cm-1): 3413, 3054, 2933 (broad peaks), 1709, 1666, 1531, 1248; 1H NMR (CDCl3) δ 1.27-1.58 (multiple peaks, 19H), 2.29 (single peak, 2H), 3.12 (double peaks, 2H, J = 6.8 Hz), 4.97 (broad peak, 1H).

References

[1] Patent: EP1157000, 2005, B1
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 4, p. 1479 - 1486
[3] Patent: WO2016/123533, 2016, A1. Location in patent: Page/Page column 40
[4] Patent: US2006/46967, 2006, A1. Location in patent: Page/Page column 134
[5] Patent: US2003/176504, 2003, A1

[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID Suppliers

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227626-60-0, [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACIDRelated Search:

(1-[(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-METHYL]-CYCLOHEXYL)-ACETIC ACID Gabapentin Related Compound E Gabapentin Related Compound D Gabapentin-D6 Gabapentin EP Impurity G IMp. A (EP): 2-Azaspiro[4.5]decan-3-one(3,3-PentaMethylene-4-butyrolactaM) Gabapentin Gabapentin impurity G Gabapentin Related Compound D Gabapentin Impurity 6 Cyclohexaneacetic acid, 1-(aMinoMethyl)-, Methyl ester GABAPENTIN-D6 HYDROCHLORIDE Cyclohexaneacetic acid, 1-[[[2-[1-(aminomethyl)cyclohexyl]acetyl]amino]methyl]- Tablet-level gabapentin Gabapentin capsule Gabapentin-d6 HCl Cyclohexylacetic acid [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID

2-N-BOC-AMINOMETHYL-2-CYCLOHEXYLACETIC ACID

[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID

[1-(N-BOC-AMINOMETHYL)-CYCLOHEXYL]-ACETIC ACID

BOC-GABAPENTIN

BOC-GPN

BOC-1-AMINOMETHYL-CYCLOHEXANE ACETIC ACID

2-[1-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclohexyl]acetic acid

2-[1-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclohexyl]ethanoic acid

Boc-2-(1-(aMinoMethyl)cyclohexyl)acetic acid

N-rt-Butyloxycarbonyl Gabapentin

Cyclohexaneacetic acid, 1-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-

2-(1-(((tert-Butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid

2-[1-[[(tert-butoxy-oxomethyl)amino]methyl]cyclohexyl]acetic acid

Gabapentin N-t-Butyloxycarbonyl

227626-60-0

pharmacetical