BOC-BETA-CYCLOHEXYL-ALA-OH Chemical Properties

Boiling point:

420.4±28.0 °C(Predicted)

Density 

1.083±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.02±0.10(Predicted)

form 

<40°C Solid,>42°C Liquid

Appearance

White to off-white <40°C Solid,>42°C Liquid

optical activity

[α]20/D 15.5±1°, c = 2% in glacial acetic acid

BRN 

3060603

InChI

InChI=1/C14H25NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h10-11H,4-9H2,1-3H3,(H,15,18)(H,16,17)/t11-/s3

InChIKey

MSZQAQJBXGTSHP-NSHDSACASA-N

SMILES

[C@H](C(=O)O)(NC(=O)OC(C)(C)C)CC1CCCCC1 |&1:0,r|

CAS DataBase Reference

37736-82-6(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

BOC-BETA-CYCLOHEXYL-ALA-OH Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

It is an agrochemical, organic and pharmaceutical intermediates.

Synthesis

Step 2. Synthesis of (S)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropionic acid. (S)-2-amino-3-cyclohexylpropanoic acid hydrochloride (118 g, 0.57 mol) was dissolved in 0.5 N NaOH aqueous solution (1200 mL), followed by the addition of a solution of tetrahydrofuran (THF, 600 mL) of di-tert-butyl dicarbonate (Boc2O, 137 g, 0.63 mol). The reaction mixture was stirred for 2 hours. After completion of the reaction, the organic solvent was removed under reduced pressure. The aqueous phase was washed with ether (Et2O, 2 x 400 mL) to remove unreacted feedstock. Subsequently, the aqueous phase was acidified to pH 5 with aqueous 2 N HCl. The acidified aqueous phase was extracted with ethyl acetate (EtOAc, 3 × 400 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give the title compound (S)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoic acid (142 g, 92%) as an oil.1H NMR (CDCl3) δ: 0.92 (m, 1H), 1.09-1.30 (m, 3H), 1.48 (s, 9H), 1.51 (m, 1H), 1.52 (m, 1H), 1.66 (m, 5H), 1.78 (m, 1H), 4.32 (m, 1H), 4.88 (m, 1H), 8.55-9.48 (br s, 1H).

References

[1] Journal of Antibiotics, 1996, vol. 49, # 9, p. 909 - 920
[2] Patent: WO2007/117557, 2007, A2. Location in patent: Page/Page column 91
[3] Patent: US5756763, 1998, A

BOC-BETA-CYCLOHEXYL-ALA-OH(37736-82-6)Related Product Information

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• BOC-D-ABU-OH
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• (S)-2-((tert-butoxycarbonyl)amino)-4-cyclohexylbutanoic acid
• Boc-D-Serine
• Boc-alpha-Cyclohexyl-D-glycine
• BOC-OIC-OH
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• BOC-L-CYCLOHEXYLALANINE HYDROXYSUCCINIMIDE ESTER
• BOC-3-CYCLOHEXYL-L-ALANINE METHYL ESTER
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• (3S,4AR,8AR)-N-BOC-DECAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
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