4-Methylmorpholine → HCID 13685962, compound

HRID 1980756Notes

Reaction equation

HRID 1980756 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.CC(C)=O>[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

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-prolineHCID 640993L-Valinol

Product 1

HCID 13685962HCID 13685962, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.98 g (20 mmol) N-carbobenzoxy-L-proline, 2.73 g (20 mmol) isobutyl chloroformate, 2.02 g (20 mmol) N-methylmorpholine, and 2.73 g (26.5 mmol) L-valinol were contacted and reacted in THF, using a mixed anhydride procedure substantially as described in Example 1. The crude product, 5.93 g, was recrystallized from a mixture of 150 mL ethyl acetate and 250 mL n-hexane to give 5.24 g (15.7 mmol, 78%) of colorless N-carbobenzoxy-L-prolyl-L-valinol, m.p. 109.3°-110.7°, α25D -65.3°, (C=1.01 g/100 mL in acetone).

Workup

  1. customThe crude product, 5.93 g, was recrystallized from a mixture of 150 mL ethyl acetate and 250 mL n-hexane

Sources & evidence

ORD record
ord-1b2abfaaa07249c39074f980e2d428fe
Source dataset
uspto-grants-1985_04
Patent number
US04511390

Reaction notes

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