Morpholine → HCID 22865437, compound

HRID 742983Notes

Reaction equation

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

Participants

Reactant 2

HCID 8083Morpholine

HCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

Product 1

HCID 22865437HCID 22865437, compoundYield 95%

Procedure

In substantially the same manner as in Example 5, morpholine (280 μl) was condensed with Boc-L-homophenylalanine (900 mg, manufactured by Bachem Fein Chemikalien AG, Switzerland) to give N-(BOC-L-homophenylalanyl)morpholine (1.06 g) as a white powder (yield 95%). After Boc group elimination with 4N HCl/ethyl acetate, the product was condensed with (2S,3S)-ethyl hydrogen trans-epoxysuccinate (338 mg) as obtained in Reference Example 8 to yield the title compound (compound 65; 630 mg) as a white powder (yield 77%).

Sources & evidence

ORD record: ord-b4b05258a4dd4f4985b69d93447ba640
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556853

Reaction notes

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