4-Methylmorpholine → HCID 69156110, compound

HRID 854283Notes

Reaction equation

HRID 854283 reaction equation
ClC(OCC(C)C)=O.[C:9]([O:13][C:14]([NH:16][C@H:17]([CH2:22][C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=1[F:31])[CH2:18][C:19]([OH:21])=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].CN1CCOCC1.[CH3:39][C@H:40]1[NH:46][CH2:45][CH2:44][C@@H:43]([CH3:47])[NH:42][C:41]1=[O:48]>ClCCl.CO.ClCCl>[C:9]([O:13][C:14]([NH:16][C@H:17]([CH2:22][C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=1[F:31])[CH2:18][C:19]([N:46]1[CH2:45][CH2:44][C@@H:43]([CH3:47])[NH:42][C:41](=[O:48])[C@H:40]1[CH3:39])=[O:21])=[O:15])([CH3:10])([CH3:11])[CH3:12]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid2×HCID 55300257HCID 55300257, compound

Product 1

HCID 69156110HCID 69156110, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

Isobutyl chloroformate (0.085 mL, 0.63 mmol) was added to a solution of (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (Intermediate 3, 210 mg, 0.63 mmol) and N-methylmorpholine (0.080 mL, 0.7 mmol) in 10 mL of dichloromethane at −20 to −30° C. and the resultant mixture was stirred for 1 h. A solution of (3R,7R)-3,7-dimethyl-1,4-diazepan-2-one in dichloromethane (5 mL) was added to the above solution. The reaction mixture was allowed to warm up to room temperature and stirring was continued overnight. The solution was subjected directly to flash chromatography on a Biotage® system (silica gel, 5% methanol/dichloromethane) to yield the title compound as a white solid. MS 358 (M−Boc+1).

Sources & evidence

ORD record
ord-57670d6164044f9f8a4229587a874e0a
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

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