BOC-D-DAP-OH Chemical Properties

Melting point:

200-203℃

Boiling point:

364.4±37.0 °C(Predicted)

Density 

1.189±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

2.88±0.16(Predicted)

form 

solid

color 

White

optical activity

Consistent with structure

InChI

InChI=1S/C8H16N2O4/c1-8(2,3)14-7(13)10-5(4-9)6(11)12/h5H,4,9H2,1-3H3,(H,10,13)(H,11,12)/t5-/m1/s1

InChIKey

KRJLRVZLNABMAT-RXMQYKEDSA-N

SMILES

C(O)(=O)[C@@H](CN)NC(OC(C)(C)C)=O

Safety Information

HazardClass 

IRRITANT

HS Code 

29225090

BOC-D-DAP-OH Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

N(alpha)-Boc-D-2,3-diaminopropionic acid is used as pharmaceutical intermediate.

Synthesis

N-Boc-L-asparagine (13; 3.48 g, 15 mmol) was used as starting material, which was co-dissolved with PIDA (5.81 g, 18 mmol) in a solvent mixture of EtOAc, MeCN, and H2O (2:2:1, v/v, total volume 62.5 mL). The reaction was carried out at 16°C for 30 min. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued for 4 hours. A precipitate was generated during the reaction, which was collected by filtration and dried to afford the target product (R)-3-amino-2-((tert-butoxycarbonyl)amino)propionic acid in a yield of 2.02 g (66% yield, 9.89 mmol) as a colorless solid with a melting point of 211-213 °C (literature value 216 °C). The product was confirmed by 1H NMR (500 MHz, DMSO-d6): δ= 1.40 [s, 9H, C(CH3)3], 2.76 (dd, 3J = 9.2 Hz, 2J = 11.8 Hz, 1H, CH2), 3.06 (dd, 3J = 5.1 Hz, 2J = 11.8 Hz, 1H, CH2), 3.65-3.69 (m 1H, COCH), 6.08 (s, 1H, OCONH). No proton signals were observed for the COOH and NH2 groups.13C NMR (125 MHz, DMSO-d6) data: δ = 28.3, 40.8, 51.1, 78.2, 155.2, 171.2. LC-MS (ESI) analysis showed 100% purity of the product; m/z = 205.19 ([M + H]+), 203.09 ([ M - H]-). HRMS (ESI+) analysis results: calculated value C8H16N2O4 ([M + H]+) m/z = 205.1183; measured value: 205.1177.

References

[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 6, p. 1629 - 1633
[2] Chemical Communications, 2011, vol. 47, # 4, p. 1198 - 1200
[3] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5696 - 5704
[4] Synlett, 2008, # 4, p. 513 - 516
[5] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214

BOC-D-DAP-OH(76387-70-7)Related Product Information

• (R)-N-Boc-piperazine-2-carboxylic acid methyl ester
• (R)-N-1-BOC-N-4-CBZ-2-PIPERAZINE CARBOXYLIC ACID
• (R)-1-N-BOC-4-N-FMOC-2-PIPERAZINE CARBOXYLIC ACID
• (R)-4-Boc-Piperazine-3-carboxylic acid
• Boc-Dap-OH
• 2,3-Diaminopropionic acid
• BOC-D-DAP(DNP)-OH
• BOC-D-DAP(ALOC)-OH DCHA
• BOC-D-DAP(DDE)-OH
• (R)-1-N-BOC-4-N-BOC-PIPERAZINE-2-CARBOXYLIC ACID
• BOC-BETA-IMIDAZOLYL-D-ALA
• BOC-D-DAP(BOC)-OH DCHA
• BOC-D-DAP(ALLOC)-OH
• N-ALPHA-BOC-(R)-2-AMINO-3-(DIMETHYLAMINO)PROPIONIC ACID
• (R)-2-TERT-BUTOXYCARBONYLAMINO-3-PYRAZOL-1-YL-PROPIONIC ACID
• BOC-D-DAP(CL-Z)-OH DCHA
• BOC-D-DAP(Z)-OH DCHA
• BOC-D-DAP-OH