Morpholine → N-[Boc-3-(2-naphthyl)-L-alanyl]morpholine

HRID 742990Notes

Reaction equation

HRID 742990 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([NH:14][C@H:15]([C:27](O)=[O:28])[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>>[C:7]([NH:14][C@H:15]([C:27]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:28])[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 7020908Boc-3-(2-naphthyl)-L-alanine

Product 1

HCID 22865433N-[Boc-3-(2-naphthyl)-L-alanyl]morpholine

Procedure

In substantially the same manner as in Example 5, morpholine (275 μl) was condensed with Boc-3-(2-naphthyl)-L-alanine (900 mg, manufactured by Bachem Fein Chemikalien AG, Switzerland) to give N-[Boc-3-(2-naphthyl)-L-alanyl]morpholine (1.10 g) as a white powder (yield quantitative). After Boc group elimination with trifluoroacetic acid, the product was condensed with (2S,3S)-ethyl hydrogen trans-epoxysuccinate as obtained in Reference Example 8 (312 mg) to yield the title compound (compound 81; 695 mg) as a white powder (yield 84%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-c90e2f6adda8412d8e9df3b1929c0f27
Source dataset
uspto-grants-1996_09
Patent number
US05556853

Reaction notes

Loading…