Morpholine → HCID 22865436, compound

HRID 742988Notes

Reaction equation

HRID 742988 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[C:1]([NH:8][C@H:9]([C:17]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Product 1

HCID 22865436HCID 22865436, compound

Procedure

In substantially the same manner as in Example 5, morpholine (210 μl) was condensed with Boc-3-cyclohexyl-L-alanine (590 mg, manufactured by Bachera Fein Chemikalien AG, Switzerland) to give N-(Boc-3-cyclohexyl-L-alanyl)morpholine (702 mg) as a colorless oily product (yield 95%). 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 (210 mg) to yield the title compound (compound 75; 379 mg) as a colorless oily product (yield 76%).

Sources & evidence

ORD record
ord-c1d2626eaf7a43c190b16764b1f5d373
Source dataset
uspto-grants-1996_09
Patent number
US05556853

Reaction notes

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