Dicyclohexylcarbodiimide → Ethyl (2S,3S)-3-[(alpha-benzylphenethyl)carbamoyl]oxirane-2-carboxylate

HRID 1456614Notes

Reaction equation

HRID 1456614 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[O:8][C@@H:7]1[C:9]([OH:11])=O)=[O:5])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:27]([CH:34]([NH2:42])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:35]([CH:34]([NH:42][C:9]([C@H:7]1[O:8][C@@H:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:11])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 779601,3-Diphenyl-2-aminopropaneHCID 11030109(2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid

Product 1

HCID 86753400Ethyl (2S,3S)-3-[(alpha-benzylphenethyl)carbamoyl]oxirane-2-carboxylate

Procedure

The reactions and treatments of Example 1 were repeated using (2S,3S)-3-ethoxycarbonyloxirane-2-carboxylic acid (1.01 g, 6.31 mmol.), N-hydroxysuccimide (726 mg, 6.31 mmol.), N,N'-dicyclohexylcarbodiimide (1.30 g, 6.31 mmol.), and α-benzylphenethylamine (1.43 g, 6.31 mmol.). Thus prepared product was purified by silica gel column chromatography (chloroform/methanol=50/1) to give the desired compound as a pale yellow oil (2.22 g, yield: quantitatively).

Workup

  1. customThus prepared product was purified by silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-abae2caab4d44791b21baf8403a9f7ce
Source dataset
uspto-grants-1998_12
Patent number
US05843992

Reaction notes

Loading…