Morpholine → HCID 22865442, compound

HRID 742986Notes

Reaction equation

[C:1]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[C:1]([NH:8][C@H:9]([C:20]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

Reactant 2

HCID 8083Morpholine

HCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 22865442HCID 22865442, compoundYield 96%

Procedure

In substantially the same manner as in Example 5, morpholine (290 μl) was condensed with Boc-p-nitro-L-phenylalanine (996 mg, Bachem Fein Chemikalien AG, Switzerland) to give N-(Boc-p-nitro-L-phenylalanyl)morpholine (1.22 g) as a white powder (yield 96%). 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 (465 mg) to yield the title compound (compound 71; 878 mg) as a white powder (yield 81%).

Sources & evidence

ORD record: ord-f7715ccba1f742c6a01f0a515151c424
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556853

Reaction notes

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