4-Methylmorpholine → HCID 13685987, compound

HRID 1980765Notes

Reaction equation

[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12]([OH:14])=O)=[O:9])=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.CN1CCOCC1.[NH2:35][C@H:36]([CH2:40][OH:41])[CH:37]([CH3:39])[CH3:38]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12]([NH:35][C@H:36]([CH2:40][OH:41])[CH:37]([CH3:39])[CH3:38])=[O:14])=[O:9])=[CH:18][CH:19]=1

Participants

Reactant 4

HCID 79724-Methylmorpholine

HCID 62365Isobutyl chloroformate

HCID 640993L-Valinol

HCID 53983956HCID 53983956, compound

Product 1

HCID 13685987HCID 13685987, compound

Procedure

The subject compound was prepared from 3.9 g (14.8 mmol) p-methylbenzyloxycarbonyl-L-proline, 2.0 g (14.6 mmol) isobutyl chloroformate, 1.5 g (14.8 mmol) N-methylmorpholine, and 1.5 g (14.5 mmol) L-valinol, using a procedure described in Example 1. The product, N-(p-methylbenzyloxycarbonyl)-L-prolyl-L-valinol, obtained after recrystallization from ethyl acetate/ n-hexane, melted at 122°-123.5°, α25D -61.9° (C=1.00 g/100 mL in acetone).

Sources & evidence

ORD record: ord-84e0fe8b6f91491da4eb80b01aec29fb
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04511390

Reaction notes

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