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

HRID 2297058Notes

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]([NH:17][C@H:18]([C:23]([NH:25][CH:26]([C:35](=[O:48])[CH2:36][O:37][C:38](=[O:47])[C:39]1[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:46])[CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[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]([NH:17][C@H:18]([C:23]([NH:25][CH:26]([C:35](=[O:48])[CH2:36][O:37][C:38](=[O:47])[C:39]1[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:46])[CH2:27][C:28]([OH:30])=[O:29])=[O:24])[CH2:19][CH:20]([CH3:21])[CH3:22])=[O:16]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86756362N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-5-(2,6-dichlorobenzoyl) oxy-4-oxo pentanoic acid, tert-butyl ester

Product 1

HCID 70158742N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-5-(2,6-dichlorobenzoyl)oxy-4-oxo pentanoic AcidYield 60%

Procedure

Treatment of N-[(1-methyl-3-isobutyl-indole-2-cabonyl)leucinyl]-3-amino-5-(2,6-dichlorobenzoyl) oxy-4-oxo pentanoic acid, tert-butyl ester (63 mg, 0.089 mmol) with TFA as described in Example 80 gave the titled product (34.5 mg, 60%) as a white powder. MS C32H37Cl2N3O7, [M+H]+=646, [M−H]−=644. TLC (CH2Cl2/MeOH, 90/10): Rf=0.23.

Sources & evidence

ORD record: ord-f692e9176fac4e31a5b3068b0cb026fe
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489353B2

Reaction notes

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