L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 22865438, compound

HRID 742981Notes

Reaction equation

HRID 742981 reaction equation
[S:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH:17]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:18]([C:26](O)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:29]([NH:17][C@H:18]([C:26]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][S:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3])=[O:27])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30]

Participants

3

Reactant 2

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 11254457HCID 11254457, compound

Product 1

HCID 22865438HCID 22865438, compoundYield 85.3%

Procedure

In substantially the same manner as in Example 5, N-tosyl-1,4-diaminobutane (1.27 g) was condensed with Boc-L-Phe-OH (1.47 g) to give N-(Boc-L-phenylalanyl)-N'-tosyl-1,4-diaminobutane (2.19 g) (yield 85%). After Boc group elimination with TFA, the product was condensed with (2S,3S)-ethyl hydrogen trans-epoxysuccinate (774 mg) as obtained in Reference Example 8 to yield the title compound (compound 32; 1.55 g) [yield 67%].

Sources & evidence

ORD record
ord-1213edb4a690430082a9665f8f7f6fe6
Source dataset
uspto-grants-1996_09
Patent number
US05556853

Reaction notes

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