4-Methylmorpholine → HCID 13685964, compound

HRID 1980761Notes

Reaction equation

HRID 1980761 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]([CH2:39][OH:40])[CH:36]([CH3:38])[CH3:37]>C1COCC1>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@@H:12]1[C:13]([NH:34][C@H:35]([CH2:39][OH:40])[CH:36]([CH3:38])[CH3:37])=[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 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylateHCID 640993L-Valinol

Product 1

HCID 13685964HCID 13685964, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.49 g (10 mmol) N-carbobenzoxy-D-proline, 1.37 g (10 mmol) isobutyl chloroformate, 1.01 g (10 mmol) N-methylmorpholine, and 1.03 g (10 mmol) L-valinol were contacted and reacted in THF substantially according to the procedure described in Example 1. Crude product (2.82 g) was recrystallized from a mixture of 20 mL ethyl acetate and 15 mL n-hexane, to give 2.37 g (7.1 mmol, 71%) of colorless crystalline N-carbobenzoxy-D-prolyl-L-valinol; m.p. 117.5°-118.6°, α25D=+26.7° (C=1.02 g/100 mL in acetone).

Workup

  1. customCrude product (2.82 g) was recrystallized from a mixture of 20 mL ethyl acetate and 15 mL n-hexane

Sources & evidence

ORD record
ord-369bc8fcf9814abfba386172c8ee5878
Source dataset
uspto-grants-1985_04
Patent number
US04511390

Reaction notes

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