Sodium Hydroxide → HCID 86699851, compound

HRID 510320Notes

Reaction equation

HRID 510320 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:30]([CH3:31])=[CH:29][C:14]2[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20](C4C=CC=CC=4)[CH2:19]3)[S:17][C:13]=2[C:12]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-:39].[Na+]>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:30]([CH3:31])=[CH:29][C:14]2[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([O:39][C:11]4[CH:30]=[CH:29][CH:14]=[CH:13][CH:12]=4)[CH2:19]3)[S:17][C:13]=2[C:12]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86699852HCID 86699852, compound

Product 1

HCID 86699851HCID 86699851, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-phenylpyrrolidin-1-yl)benzo[d]thiazol-6-yl)acetate (29.3 mg, 0.653 mmol) in CH3OH (1 mL) was added NaOH (1N, 1 mL, 1 mmol), the resulting mixture was heated at 50 C for 10 hr. The mixture was acidified to pH 3 and evaporated to a small volume, and the residue was partitioned between CH2Cl2 and brine. The organic layer was separated, dried, filtered and evaporated to dryness. The residue was purified on TLC (50% EtOAc/Hex) to give (2S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-phenoxypyrrolidin-1-yl)benzo[d]thiazol-6-yl)acetic acid. LCMS-ESI+: calc'd for C30H32ClN2O3S: 534.2, 536.2 (M+H+); found: 535.2, 537.2 (M+H+). 1H-NMR: 400 MHz, (CD3OD) δ: 7.63 (dd, J=2.0, 7.2 Hz, 1H), 7.49-7.52 (m, 3H), 7.30-7.34 (m, 5H), 7.24 (m, 1H), 5.13 (s, 1H), 3.94 (m, 1H), 3.70 (m, 1H), 3.52-3.63 (m, 4H), 2.48 (s, 3H), 2.46 (m, 1H), 2.20 (m, 1H), 0.94 (s, 9H).

Workup

  1. temperaturethe resulting mixture was heated at 50 C for 10 hr
  2. customevaporated to a small volume
  3. customthe residue was partitioned between CH2Cl2 and brine
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified on TLC (50% EtOAc/Hex)

Sources & evidence

ORD record
ord-6430e184bc824cd49424bef4171d299a
Source dataset
uspto-grants-2015_08
Patent number
US09096586B2

Reaction notes

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