4-Methylmorpholine → HCID 13685969, compound

HRID 1980758Notes

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.[CH3:34][CH2:35][C@H:36]([NH2:39])[CH2:37][OH:38]>>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:39][C@H:36]([CH2:37][OH:38])[CH2:35][CH3:34])=[O:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

Reactant 4

HCID 79724-Methylmorpholine

HCID 62365Isobutyl chloroformate

HCID 101987Benzyloxycarbonyl-L-proline

HCID 1200842-Amino-1-butanol, (+)-

Product 1

HCID 13685969HCID 13685969, compound

Procedure

This compound was prepared from 4.99 g (20 mmol) N-carbobenzoxy-L-proline, 2.73 g (20 mmol) isobutyl chloroformate, 2.02 g (20 mmol) N-methylmorpholine, and 1.78 g (20 mmol) d-(+)2-amino-1-butanol, substantially according to the mixed anhydride procedure described in Example 1. Crude product (5.16 g) was recrystallized from a mixture of 60 mL ethyl acetate and 15 mL n-hexane to give 4.18 g (13 mmol, 65%) of colorless, crystalline N-carbobenzoxy-L-prolyl-L-homoalaninol; m.p. 105.4°-106.3°, α25D-69.7 (C=1.04 g/100 mL in acetone). A stereochemical assignment for this product was based upon observed similarity of specific rotation to specific rotations measured for L-L isomers of carbobenzoxy-prolyl-leucinol (Example 1), carbobenzoxy-prolyl-valinol (Example 2) and carbobenzoxy-prolyl-alaninol (Example 5).

Workup

customCrude product (5.16 g) was recrystallized from a mixture of 60 mL ethyl acetate and 15 mL n-hexane

Sources & evidence

ORD record: ord-c79ff45f23d148a0b51fe467fb150b8e
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04511390

Reaction notes

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