Sulfuric Acid → HCID 66724795, compound

HRID 1799211Notes

Reaction equation

HRID 1799211 reaction equation
[C:1]([CH:8]([C@H:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)[CH:16]=1)[CH2:13][NH2:14])[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].FC(F)(F)C(O)=[O:33].S(=O)(=O)(O)O>>[C:1]([CH:8]([C@H:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)[CH:16]=1)[CH2:13][NH2:14])[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[ClH:21].[NH2:14][CH2:13][C@@H:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28](=[O:33])[NH2:29])[CH:23]=2)[CH:16]=1)[CH2:8][C:1]([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 66724819HCID 66724819, compound

Product 2

HCID 66724795HCID 66724795, compoundHCID 66724819HCID 66724819, compound

Procedure

Boc-(3R)-4-amino-3-[4-chloro-3-(3-cyanophenyl)phenyl]butanoic acid (52a) was synthesized using the general Suzuki cross coupling procedure. Crude Boc-(3R)-4-amino-3-[4-chloro-3-(3-cyanophenyl)phenyl]butanoic acid (52a) (130 mg, 0.32 mmol) was treated with 1 mL of trifluoroacetic acid/conc. sulfuric acid (4:1) and stirred for 1 h at room temperature. Trifluoroacetic acid was removed in vacuo. The crude residue was purified by preparative HPLC to provide the title compound (52) as a white solid. 1H-NMR (400 MHz, CD3OD): δ 2.78-2.83 (m, 1H), 2.65-2.71 (m, 1H), 3.19-3.25 (dd, J=22.0, 9.2 Hz, 1H), 3.32-3.47 (m, 2H), 7.92-7.93 (m, 1H), 7.87-7.89 (d, J=7.6, 1 Hz), 7.62-7.64 (d, J=7.6 Hz, 1H), 7.51-7.54 (m, 2H), 7.32-7.38 (m, 2H); MS (ESI) m/z 333.00 (M+H)+.

Workup

  1. customTrifluoroacetic acid was removed in vacuo
  2. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7a5545a96a2c4353aec62f3fb01233a8
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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