Dicyclohexylcarbodiimide → HCID 67986785, compound

HRID 2363253Notes

Reaction equation

[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:9](O)=[O:10])=[CH:3][CH:2]=1.[CH3:26][C:27]1([CH3:35])[O:34][C:32](=[O:33])[CH2:31][C:29](=[O:30])[O:28]1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:16]([O:15][C:13](=[O:14])[NH:12][C@H:8]([CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][CH:5]=1)[C:9]([CH:31]1[C:32](=[O:33])[O:34][C:27]([CH3:35])([CH3:26])[O:28][C:29]1=[O:30])=[O:10])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: -5 °C

Procedure

To a solution of (R)-3-biphenyl-4-yl-2-t-butoxycarbonylamino-propionic acid (50 g, 146 mmol), Meldrum's acid (23.3 g, 161 mmol) and DMAP (27.8 g, 227 mmol) in anhydrous DCM (500 mL) was added a solution of DCC (33.3 g, 161 mmol) in anhydrous DCM (200 mL) over 1 hour at −5° C. under nitrogen. The mixture was stirred at −5° C. for 8 hours, then refrigerated overnight, during which tiny crystals of dicyclohexylurea precipitated. After filtration, the mixture was washed with 5% KHSO4 (4×200 mL) and saturated aqueous NaCl (1×200 mL), then dried under refrigeration with MgSO4 overnight. The solution was evaporated to yield the title compound (68 g, light yellow solid), which was used without further purification. LC-MS: 490 [M+Na], 957 [2M+Na].

Workup

customrefrigerated overnight, during which tiny crystals of dicyclohexylurea precipitated
filtrationAfter filtration
washthe mixture was washed with 5% KHSO4 (4×200 mL) and saturated aqueous NaCl (1×200 mL)
dry with materialdried under refrigeration with MgSO4 overnight
customThe solution was evaporated

Sources & evidence

ORD record: ord-4f4c58bcfbeb4621b95a2df3f3d9a4ac
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691868B2

Reaction notes

Loading…