Trifluoroacetic acid → HCID 90082942, compound

HRID 593480Notes

Reaction equation

HRID 593480 reaction equation
[F:1][C:2]([F:49])([F:48])[CH2:3][CH2:4][C@@H:5]([C:21](=[O:47])[NH:22][C@@H:23]1[C:29](=[O:30])[N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[C:27]2[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=2[C:25]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N:24]1)[C@H:6]([CH2:14][CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:7]([O:9]C(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:48][C:2]([F:1])([F:49])[CH2:3][CH2:4][C@@H:5]([C:21](=[O:47])[NH:22][C@@H:23]1[C:29](=[O:30])[N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[C:27]2[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=2[C:25]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N:24]1)[C@H:6]([CH2:14][CH2:15][CH2:16][C:17]([F:20])([F:18])[F:19])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90087892HCID 90087892, compound

Product 1

HCID 90082942HCID 90082942, compoundYield 117.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Intermediate 1C (62 mg, 0.090 mmol) in DCM (1 mL) was treated with TFA (1 mL). The reaction mixture was stirred at room temperature for 1.5 h and then concentrated to dryness to afford Intermediate 1D (67 mg, 100%). HPLC: RT=3.011 min (CHROMOLITH® ODS 4.6×50 mm (3 min grad) eluting with 10-90% aqueous MeOH over 4 minutes containing 0.% TFA, 4 mL/min, monitoring at 220 nm); MS(ES): m/z=634 [M+H]+.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b5e729d12f8f407cb1cf9c031d2df0a4
Source dataset
uspto-grants-2016_01
Patent number
US09242940B2

Reaction notes

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