Morpholine → (S)-2-(N-t-Butoxycarbonylamino)-3-(4-fluoro-phenyl)-1-morpholin-4-yl-propan-1-one

HRID 742985Notes

Reaction equation

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

Participants

Reactant 2

HCID 8083Morpholine

HCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

Product 1

HCID 22865441(S)-2-(N-t-Butoxycarbonylamino)-3-(4-fluoro-phenyl)-1-morpholin-4-yl-propan-1-oneYield 91%

Procedure

In substantially the same manner as in Example 5, morpholine (278 μl) was condensed with Boc-p-fluoro-L-phenylalanine (900 mg, manufactured by Bachera Fein Chemikalien AG, Switzerland) to give N-(Boc-p-fluoro-L-phenylalanyl)morpholine (1.02 g) as a white powder (yield 91%). 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 (333 mg) to yield the title compound (compound 69; 520 mg) as a white powder (yield 63%).

Sources & evidence

ORD record: ord-0836bb07b652428c87d7517371462e6f
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556853

Reaction notes

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