Water → Dicyclohexylcarbodiimide

HRID 1647916Notes

Reaction equation

C(OC([CH:8]([CH2:12][C:13](=O)[NH2:14])[C:9](O)=O)=O)(C)(C)C.[CH:16]1[CH:17]=[CH:18][C:19]2[N:24](O)N=N[C:20]=2[CH:21]=1.O.O1CC[CH2:29][CH2:28]1.[CH3:32]N(C)C=O>>[CH2:16]1[CH2:21][CH2:20][CH:19]([N:24]=[C:32]=[N:14][CH:13]2[CH2:12][CH2:8][CH2:9][CH2:29][CH2:28]2)[CH2:18][CH2:17]1

Participants

Reactant 4

HCID 962Water

HCID 757711-Hydroxybenzotriazole

HCID 21974620tetrahydrofuran N,N-dimethylformamide

HCID 86748795HCID 86748795, compound

Product 1

HCID 10868DicyclohexylcarbodiimideYield 85%

Procedure

The subtitled compound was prepared substantially in accordance with the procedure detailed in Example 1 using 0.50 g (1.18 mmol) of the subtitled intermediate of Preparation 1E, 0.289 g (1.24 mmol) of (2S)-2-N(t-butoxycarbonyl-3-carbamoyl propanoic acid 0.163 g (1.21 mmol) of HOBT.H2O and 0.249 g (1.21 mmol) of DCC in 11.5 mL of a 10:1.5 solution of tetrahydrofuran/dimethylformamide to provide a white solid. This solid was purified using flash chromatography (gradient eluent of 1-5% methanol in methylene chloride) to provide 0.64 g of the desired subtitled compound.

Sources & evidence

ORD record: ord-1469640e0bf34bc9b918109e82ed1996
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05434265

Reaction notes

Loading…