Trifluoroacetic acid → N-[(1-methyl-3-isobutyl-indole-2-cabonyl)cyclohexylalaninyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid

HRID 2297060Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:3]1[C:15]([N:17]([CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)[C@H:18]([C:20]([NH:22][CH:23]([C:32](=[O:45])[CH2:33][O:34][C:35]1[C:40]([F:41])=[C:39]([F:42])[CH:38]=[C:37]([F:43])[C:36]=1[F:44])[CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:21])[CH3:19])=[O:16].C(O)(C(F)(F)F)=O>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:3]1[C:15]([N:17]([CH:46]1[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1)[C@H:18]([C:20]([NH:22][CH:23]([C:32](=[O:45])[CH2:33][O:34][C:35]1[C:36]([F:44])=[C:37]([F:43])[CH:38]=[C:39]([F:42])[C:40]=1[F:41])[CH2:24][C:25]([OH:27])=[O:26])=[O:21])[CH3:19])=[O:16]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86756365N-[(1-methyl-3-isobutyl-indole-2-cabonyl)cyclohexylalaninyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Product 1

HCID 20639706N-[(1-methyl-3-isobutyl-indole-2-cabonyl)cyclohexylalaninyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid

Procedure

Treatment of N-[(1-methyl-3-isobutyl-indole-2-cabonyl)cyclohexylalaninyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester with TFA as described in Example 80 gave the titled product (55.5 mg) as a white powder. MS C34H39F4N3O6, [M+Na]+=684, [M−H]−=660. TLC (CH2Cl2/MeOH, 90/10): Rf=0.24.

Sources & evidence

ORD record: ord-98232ec09d6747189a9ad365016b2046
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489353B2

Reaction notes

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