4-Methylmorpholine → HCID 13685967, compound

HRID 1980757Notes

Reaction equation

HRID 1980757 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].ClC(OCC(C)C)=O.CN1CCOCC1.[NH2:34][C@H:35]([CH2:37][OH:38])[CH3:36]>C1COCC1>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:34][C@H:35]([CH2:37][OH:38])[CH3:36])=[O:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 80307L-AlaninolHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 13685967HCID 13685967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.98 g (20 mmol) N-carbobenzoxy-L-proline, 2.73 g (20 mmol) isobutyl chloroformate, 2.02 g (20 mmol) N-methylmorpholine, and 1.50 g (20 mmol) L-alaninol were contacted and reacted in THF substantially according to the mixed anhydride procedure described in Example 1. Recrystallization of crude product from 50 ml ehtyl acetate provided 3.61 g (11.8 mmol, 59%) of colorless, crystalline N-carbobenzoxy-L-prolyl-L-alaninol; m.p. 126.5°-127.6°, α25D-48.9° (C=1.03 g/100 mL in acetone).

Workup

  1. customRecrystallization of crude product from 50 ml ehtyl acetate

Sources & evidence

ORD record
ord-7edc6e203a8a4bc4af1111821162e66c
Source dataset
uspto-grants-1985_04
Patent number
US04511390

Reaction notes

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