4-Methylmorpholine → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester

HRID 1719447Notes

Reaction equation

CN1CC[O:5][CH2:4][CH2:3]1.ClC(O[CH2:12][CH:13]([CH3:15])[CH3:14])=O.C([CH2:23][C@H:24]([NH2:28])[C:25]([OH:27])=[O:26])C[C@@H](N)C(O)=O.NC[C:31]([OH:33])=[O:32].C[Si]([CH:38]([Si](C)(C)C)[C:39]([NH2:41])=[O:40])(C)C>ClCCl.CN(C)C=O>[NH:28]([C:31]([O:33][C:13]([CH3:12])([CH3:14])[CH3:15])=[O:32])[C@@H:24]([C:25]([O:27][N:41]1[C:4](=[O:5])[CH2:3][CH2:38][C:39]1=[O:40])=[O:26])[CH3:23]

Participants

Conditions

Temperature: -40 °C

Procedure

To a mixture of Compound (1) (560 mg.) and N-methylmorpholine (202 mg.) in dichloromethane (30 ml.), there was added isobutyl chloroformate (273 mg.) at -15°--20° C. and the mixture was stirred for 30 minutes at the same temperature. The mixture was cooled to -40° C. and, to this, there was added trimethylsilyl ester of Compound (2), which was prepared from Compound (2) (910 mg.) and bis(trimethylsilyl)acetamide (3 ml.) by stirring in a mixture of dichloromethane (20 ml.) and N,N-dimethylformamide (2 ml.). The mixture was stirred for 1 hour at -15°--20° C., and then treated in the same manner as the Step 1 of Example 57 to give Compound 3 (1.8 g.).

Workup

stirringThe mixture was stirred for 1 hour at -15°--20° C.
additiontreated in the same manner as the Step 1 of Example 57

Sources & evidence

ORD record: ord-f75f43994387484097057876ba4ef898
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539155

Reaction notes

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