Dicyclohexylcarbodiimide → Tert-butyl (2s)-2-(benzyloxycarbonylamino)-3-(4-(methoxycarbonylmethyloxy)benzoylamino)propionate

HRID 2297388Notes

Reaction equation

[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:4].ON1C2C=CC=CC=2N=N1.[NH2:26][CH2:27][C@H:28]([NH:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:40]([O:39][C:37]([NH:36][C@@H:28]([CH2:27][NH:26][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:15][CH:14]=1)[C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[O:38])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

Conditions

Temperature: 0 °C

Procedure

420 mg (0.002 mol) of 4-(methoxycarbonylmethyloxy)benzoic acid, 270 mg (0.002 mol) of 1-hydroxybenzotriazole and 588 mg (0.002 mol) of tert-butyl (2S)-3-amino-2-benzyloxycarbonylaminopropionate were dissolved in 5 ml of dimethylformamide. The solution was cooled to 0° C. and treated with 453 mg (0.0022 mol) of N,N′-dicyclohexylcarbodiimide and then stirred at 0° C. for 10 min and at room temperature for 2 h. For working-up, the urea was filtered off and the filtrate was concentrated to dryness. The pure compound was obtained by chromatography of the crude product on silica gel (dichloromethane/acetonitrile 20/1). Yield: 820 mg.

Workup

filtrationthe urea was filtered off
concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record: ord-095ea15eb3e24a80802b43a9461d1248
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492356B1

Reaction notes

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