Diisopropylethylamine → N,N'-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid

HRID 38052Notes

Reaction equation

HRID 38052 reaction equation
[OH:1][C@@H:2]([CH2:6][CH2:7]N)[C:3]([OH:5])=[O:4].[CH2:9]([O:16][C:17]([NH:19][C:20]([N:32]1C=CC=N1)=[N:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:17]([N:19]([CH2:7][CH2:6][C@H:2]([OH:1])[C:3]([OH:5])=[O:4])[C:20]([NH2:32])=[N:21][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])([O:16][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27339294-Amino-2-hydroxybutyric acid, (S)-(-)-HCID 3563804Phenylmethyl N-((((phenylmethoxy)carbonyl)amino)-1H-pyrazol-1-ylmethylene)carbamate

Product 1

HCID 66728201N,N'-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 2(S)-hydroxy-4-amino-butyric acid (0.059 g, 0.50 mmol) in DMF (2 ml) was added N,N′-bis(benzyloxycarbonyl)-1 H-pyrazole-1-carboxamidine (0.26 g, 0.70 mmol) followed by DIPEA (0.87 mL, 4.99 mmol) and the reaction was heated to 80° C. and stirred overnight. The crude mixture was purified on a 2-inch reverse-phase HPLC column to yield N,N′-bis-Cbz-2(S)-hydroxy-4-guanidino-butyric acid: MS: m/z, (M+H)+ calcd. 430.15, found 430.1.

Workup

  1. customThe crude mixture was purified on a 2-inch reverse-phase HPLC column

Sources & evidence

ORD record
ord-7ba752991f1d419b8890f853aebbc699
Source dataset
uspto-grants-2013_09
Patent number
US08524675B2

Reaction notes

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