Morpholine → N-(Boc-p-chloro-L-phenylalanyl)morpholine

HRID 742984Notes

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]([Cl: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]([Cl:23])=[CH:21][CH:22]=1)([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]

Participants

Reactant 2

HCID 8083Morpholine

HCID 2734499N-(tert-Butoxycarbonyl)-4-chloro-L-phenylalanine

Product 1

HCID 22865440N-(Boc-p-chloro-L-phenylalanyl)morpholine

Procedure

In substantially the same manner as in Example 5, morpholine (257 μl) was condensed with Boc-p-chloro-L-phenylalanine (800 mg, manufactured by Bachem Fein Chemikalien AG, Switzerland) to give N-(Boc-p-chloro-L-phenylalanyl)morpholine (913 mg) as a colorless oily product (yield 93%). After Boc group elimination with 4N HCl/ethyl acetate, the product was condensed with (2S,3S)-ethyl hydrogen trans-epoxysuccinate (238 mg) as obtained in Reference Example 8 to yield the title compound (compound 67; mg) as a white powder (yield 58%).

Sources & evidence

ORD record: ord-92c553f7b8dd4ac1820e8b6380303536
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556853

Reaction notes

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