4-Methylmorpholine → HCID 13685985, compound

HRID 1980764Notes

Reaction equation

[Cl: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]>>[Cl: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 54054513HCID 54054513, compound

Product 1

HCID 13685985HCID 13685985, compound

Procedure

The subject compound was prepared from 0.85 g (2.98 mmol) p-chlorobenzyloxycarbonyl-L-proline, 0.41 g (2.98 mmol) isobutyl chloroformate, 0.30 g (2.97 mmol) N-methylmorpholine, and 0.31 g (2.98 mmol) L-valinol, substantially according to the mixed anhydride procedure described in Example 1. N-(p-chlorobenzyloxycarbonyl)-L-prolyl-L-valinol obtained after recrystallization from ethyl acetate/n-hexane melted at 143°-144.5°.

Sources & evidence

ORD record: ord-048f0ac4e90841e49a25bf081e119550
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04511390

Reaction notes

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