Sodium Hydroxide → HCID 68284310, compound

HRID 1527576Notes

Reaction equation

HRID 1527576 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:35](=[O:37])[CH3:36])=[CH:10][N:11]2[CH2:14][C:15]([N:17]2[CH2:21][C@H:20]([F:22])[CH2:19][C@H:18]2[C:23](=[O:34])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[F:33])=[O:16])=[CH:7][CH:6]=1.[OH-].[Na+]>C1COCC1.O>[C:35]([C:9]1[C:8]2[C:12](=[CH:13][C:5]([CH2:4][C:3]([OH:38])=[O:2])=[CH:6][CH:7]=2)[N:11]([CH2:14][C:15]([N:17]2[CH2:21][C@H:20]([F:22])[CH2:19][C@H:18]2[C:23](=[O:34])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[F:33])=[O:16])[CH:10]=1)(=[O:37])[CH3:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68283689HCID 68283689, compound

Product 1

HCID 68284310HCID 68284310, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-acetyl-1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-1H-indol-6-yl)-acetic acid methyl ester Example 549 (200 mg, 0.366 mmol) in THF (5 mL) and water (0.5 mL) was added 1N NaOH (1.46 mL, 1.46 mmol) and the reaction was stirred at RT for 60 h. The mixture was partitioned between diethylether and water. The layers were separated and the aqueous phase was adjusted to pH=2 by addition of a 1N HCl solution to form a precipitate. The solid was filtered off, washed with water diethylether and dried in vacuo to afford the title compound as a solid. MS (LC/MS): 532 [M+H]+; tR (HPLC conditions k): 3.19 min.

Workup

  1. customThe mixture was partitioned between diethylether and water
  2. customThe layers were separated
  3. additionthe aqueous phase was adjusted to pH=2 by addition of a 1N HCl solution
  4. customto form a precipitate
  5. filtrationThe solid was filtered off
  6. washwashed with water diethylether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-989b38f5ecc742c3be10ad13bb876ffa
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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