Diisopropylethylamine → HCID 131723228, compound

HRID 1937814Notes

Reaction equation

[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH:8]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[C:9]([OH:11])=O)=[CH:5][CH:4]=1)#[N:2].[CH3:19][O:20][C:21]([C@@H:23]([NH2:30])[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22].Cl.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:19][O:20][C:21](=[O:22])[C@@H:23]([NH:30][C:9](=[O:11])[CH:8]([C:12](=[O:13])[N:14]([CH3:16])[CH3:15])[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:18][CH:17]=1)[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

Conditions

Temperature: -10 °C

Procedure

2-(R,S)-(4-Cyano-benzyl)-N,N-dimethyl-malonamic acid (10 g, 40.6 mmol) and L-cyclohexylglycine methylester hydrochloride (8.3 g, 40 mmol) were dissolved in dimethylformamide (500 ml). After cooling to −10° C. TOTU (13.1 g, 40 mmol) and diisopropylethylamine (10.34 g, 80 mmol) were added. The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation ethyl acetate was added to the residue and the organic layer was extracted with aqueous sodium hydogen carbonate solution, potassium hydrogen sulfate solution and water. The organic layer was evaporated. Yield: 14.53 g (90%); MS m/z: 400.3 (M+H)+.

Workup

temperatureto warm to room temperature
customAfter evaporation ethyl acetate
additionwas added to the residue
extractionthe organic layer was extracted with aqueous sodium hydogen carbonate solution, potassium hydrogen sulfate solution and water
customThe organic layer was evaporated

Sources & evidence

ORD record: ord-6da3d8a95b41443bbc9f7fa99ce9cd3b
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06395737B1

Reaction notes

Loading…