Trifluoroacetic acid → HCID 67827898, compound

HRID 2248506Notes

Reaction equation

HRID 2248506 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:20]([NH:22][C:23]2[CH:24]=[C:25]([CH:56]=[CH:57][CH:58]=2)[C:26]([NH:28][C@H:29]([C:38]([NH:40][C@H:41]([C:53]([OH:55])=[O:54])[CH2:42][C:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH:46]=[CH:45][CH:44]=2)=[O:39])[CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])=[O:27])=[O:21])[NH:12]C(OC(C)(C)C)=O)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62]>C(Cl)Cl>[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62].[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:20]([NH:22][C:23]2[CH:24]=[C:25]([CH:56]=[CH:57][CH:58]=2)[C:26]([NH:28][C@H:29]([C:38]([NH:40][C@H:41]([C:53]([OH:55])=[O:54])[CH2:42][C:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH:46]=[CH:45][CH:44]=2)=[O:39])[CH2:30][C:31](=[O:32])[OH:33])=[O:27])=[O:21])[NH2:12])=[CH:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54549046HCID 54549046, compound

Product 1

HCID 67827898HCID 67827898, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 55 mg of N-[N-[m-[[3-(p-amidinophenyl)-N-(t-butoxycarbonyl)-DL-alanyl]amino]benzoyl]-3-(t-butoxycarbonyl)-L-alanyl]-3-(1-naphthyl)-L-alanine (1:1 epimer) in a mixture of 10 ml of methylene chloride and 5 ml of trifluoroacetic acid is held at room temperature for 2 hours while gassing with argon. After evaporation of the solvent there is obtained N-[N-[m-[[3-(p-amidinophenyl)-DL-alanyl]amino]benzoyl]-L-α-aspartyl]-3-(1-naphthyl)-L-alanine trifluoroacetate (1:2), m.p. 165° C. (dec.) (ethanol/ethyl acetate), yield: 84% of theory, MS: 639 (M+H)+.

Workup

  1. customAfter evaporation of the solvent there

Sources & evidence

ORD record
ord-97361fdafb1741939e61e780e51c5cf3
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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