Trifluoroacetic acid → HCID 90082754, compound

HRID 2276879Notes

Reaction equation

HRID 2276879 reaction equation
[F:1][C:2]([F:44])([F:43])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:42])[NH:21][CH:22]1[C:28](=[O:29])[NH:27][C:26]2[C:30]([CH3:34])=[CH:31][CH:32]=[CH:33][C:25]=2[C:24]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[N:23]1)[C@H:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([O:9]C(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>ClCCl>[F:44][C:2]([F:1])([F:43])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:42])[NH:21][CH:22]1[C:28](=[O:29])[NH:27][C:26]2[C:30]([CH3:34])=[CH:31][CH:32]=[CH:33][C:25]=2[C:24]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[N:23]1)[C@H:6]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90083066HCID 90083066, compound

Product 1

HCID 90082754HCID 90082754, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (2R,3R)-tert-butyl 6,6,6-trifluoro-3-((5-(3-fluorophenyl)-9-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamoyl)-2-phenylhexanoate (168 mg, 0.275 mmol) in dichloromethane (2 mL) was treated with TFA (2 mL) and allowed to stand at room temperature for 3 hours. The mixture was diluted with DCM and evaporated to dryness. The residue was dissolved in DCM and washed with water and concentrated to give (2R,3R)-6,6,6-trifluoro-3-((5-(3-fluorophenyl)-9-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl) carbamoyl)-2-phenylhexanoic acid as a light-yellow off-white solid. MS(ES):m/z=556.1 [M+H+].

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d930675960734fd9bc81d207bcee6c4c
Source dataset
uspto-grants-2015_09
Patent number
US09133139B2

Reaction notes

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