4-Methylmorpholine → HCID 13685970, compound

HRID 1980759Notes

Reaction equation

HRID 1980759 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(O[CH2:23][CH:24](C)C)=O.C[N:28]1[CH2:33][CH2:32][O:31]CC1>C1COCC1>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:28][C@@H:33]([CH2:32][OH:31])[CH2:23][CH3:24])=[O:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

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

Product 1

HCID 13685970HCID 13685970, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.98 g (20 mmol) N-carbobenzoxy-L-proline, 2.73 g (20 mmol) isobutyl chloroformate, 2.03 g (20 mmol) N-methylmorpholine, and 1.78 g (20 mmol) 1-(-)-2-amino-1-butanol were contacted and reacted in THF substantially according to the mixed anhydride procedure described in Example 1. The resulting crude product, 5.58 g, was recrystallized from a mixture of 40 mL ethyl acetate and 60 mL n-hexane, providing 3.87 g (12.1 mmol, 60.4%) of colorless crystalline N-carbobenzoxy-L-prolyl-D-homoalaninol; m.p. 99.5°-101.5°, α25D-28.5° (C=1.00 g/100 mL of acetone).

Workup

  1. customThe resulting crude product, 5.58 g, was recrystallized from a mixture of 40 mL ethyl acetate and 60 mL n-hexane

Sources & evidence

ORD record
ord-d373bd7b9da1482c9142bdc915155ec3
Source dataset
uspto-grants-1985_04
Patent number
US04511390

Reaction notes

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