Dichloromethane → 4-Methylmorpholine

HRID 1597759Notes

Reaction equation

HRID 1597759 reaction equation
[N:1]1([C:14]([O:16][CH2:17][C:18]2[CH:23]=CC=C[CH:19]=2)=[O:15])[CH2:13][CH2:12]C[C@H:2]1[C:3](N[C@H](C(O)=O)C)=[O:4].C(Cl)[Cl:25]>>[CH2:17]([O:16][C:14]([Cl:25])=[O:15])[CH:18]([CH3:23])[CH3:19].[CH3:14][N:1]1[CH2:2][CH2:3][O:4][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 73513N-Benzyloxycarbonyl-L-prolyl-L-alanine

Product 2

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformate

Procedure

A suspension of 1.600 g (5.0 mmoles) of Z-(L)-Pro-(L)-AlaOH (Sigma) in 80 ml of dry methylene chloride (CH2Cl2) was brought in an argon atmosphere to a temperature of approximately -20° C. On stabilization of the temperature, the following were added in quick succession: 0.670 ml (5.13 mmoles) of isobutylchloroformate (IBCF) and 0.570 ml (5.17 mmoles) of 4-methylmorpholine (NMM), leaving the system under stirring for approximately 2 minutes.

Workup

  1. customwas brought in an argon atmosphere to a temperature of approximately -20° C
  2. additionOn stabilization of the temperature, the following were added in quick succession

Sources & evidence

ORD record
ord-c9d862844a164e7ab4447bd4abcae770
Source dataset
uspto-grants-1998_04
Patent number
US05736518

Reaction notes

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