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

HRID 742987Notes

Reaction equation

HRID 742987 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([NH:14][C@H:15]([C:22](O)=[O:23])[CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>>[C:7]([NH:14][C@H:15]([C:22]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:23])[CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 27344843-(Thien-2-yl)-L-alanine, N-BOC protected

Product 1

HCID 22865434N-[Boc-3-(2-thienyl)-L-alanyl]morpholine

Procedure

In substantially the same manner as in Example 5, morpholine (319 μl) was condensed with Boc-3-(2-thienyl)-L-alanine (900 mg, manufactured by Bachem Fein Chemikalien AG, Switzerland) to give N-[Boc-3-(2-thienyl)-L-alanyl]morpholine (1.13 g) as a colorless oily product (yield quantitative). After Boc group elimination with 4N HCl/ethyl acetate, the product was condensed with (2S,3S)-ethyl hydrogen trans-epoxysuccinate as obtained in Reference Example 8 (315 mg) to yield the title compound (compound 73; 563 mg) as a white powder (yield 75%).

Sources & evidence

ORD record
ord-73f06a27286440c797b77399d5f2893d
Source dataset
uspto-grants-1996_09
Patent number
US05556853

Reaction notes

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