Sodium Hydroxide → HCID 67350881, compound

HRID 1669511Notes

Reaction equation

HRID 1669511 reaction equation
C[O:2][C:3](=[O:39])[C@@H:4]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[OH-].[Na+]>C1COCC1.O>[C:35]([O:34][C:32]([NH:31][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)=[CH:24][CH:25]=3)=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)[C:3]([OH:39])=[O:2])=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67352711HCID 67352711, compound

Product 1

HCID 67350881HCID 67350881, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of the product from step 6 (0.4 g, 0.72 mmol) and NaOH (62 mg, 1.54 mmol) in THF/water (1:1, 10 mL) was stirred at room temperature for 16 h. After the THF was removed, the aqueous solution was acidified with 10% HCl to pH=2, the solid was collected on a filter to yield the title compound (340 mg, 82%). 1HNMR (CDCl3) δ 1.42 (s, 9H), 3.15 (m, 2H), 4.57 (m, 1H), 5.00 (m, 1H), 6.95 (d, J=8.8 Hz, 2H), 7.02-7.15 (m, 6H), 7.17 (d, J=8.8 Hz, 2H), 7.30 (d, J=3.2 Hz, 1H), 7.85 (d, J=3.2 Hz, 1H), 7.91 (d, J=8.8 Hz, 2H).

Workup

  1. customAfter the THF was removed
  2. customthe solid was collected on
  3. filtrationa filter

Sources & evidence

ORD record
ord-06bdad53da1541b9a336865510a32c97
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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