4-Hydroxybenzoic Acid → 4-Hydroxybenzoyl-(2S)-2-benzyloxycarbonylamino-beta-alanine tert-butyl ester

HRID 612854Notes

Reaction equation

HRID 612854 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH2:11][CH2:12][C@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:17]([O:16][C:14](=[O:15])[C@@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:12][NH:11][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

Product 1

HCID 153806404-Hydroxybenzoyl-(2S)-2-benzyloxycarbonylamino-beta-alanine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.41 g (10.2 mmol) of 4-hydroxybenzoic acid and 3 g (10.2 mmol) of (1.1) were suspended in 25 ml of DMF. 1.38 g (10.2 mmol) of 1-hydroxy-benzotriazole (HOBt) and, at 0° C., dicyclohexylcarbodiimide (DCCI) were added. The mixture was stirred at 0° C. for 1 h and allowed to stand at room temperature overnight. After filtration, the solvent was removed in vacuo and the residue was chromatographed on silica gel by means of MPLC using heptanelethyl acetate (1/1). (1.2) was obtained as a colorless solid; melting point 69° C.

Workup

  1. waitto stand at room temperature overnight
  2. filtrationAfter filtration
  3. customthe solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel by means of MPLC

Sources & evidence

ORD record
ord-86436cf819b44b73973f891ebe26eac8
Source dataset
uspto-grants-1999_12
Patent number
US06005117

Reaction notes

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