Water → HCID 18373470, compound

HRID 2301596Notes

Reaction equation

HRID 2301596 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:29]([O:31]C)=[O:30])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:15]([C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[C:20]([N+:25]([O-:27])=[O:26])[C:19]=1Cl)(=[O:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[OH2:35]>>[C:1]([O:5][C:6]([NH:8][CH:9]([C:29]([OH:31])=[O:30])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:15]([C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[C:20]([N+:25]([O-:27])=[O:26])[C:19]=1[OH:35])(=[O:17])=[O:16])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 18373457HCID 18373457, compound

Product 1

HCID 18373470HCID 18373470, compoundYield 76%

Procedure

Following the general hydrolysis procedure outlined in example 15, N-[5-(tert-butoxycarbonylamino)-5-methoxycarbonylpentyl]-2,6-dichloro-3-nitrobenzenesulfonamide (1.2 g, 2.33 mmol), 60% NaH (379 mg, 9.32mmol) and water (84 μL, 4.66 mmol) were reacted to form the desired product (850 mg, 76%). 1H NMR (MeOD-d4): δ 8.05 (d, 1H), 7.22 (d, 1H), 4.00 (m, 1H), 3.01 (t, 2H), 1.72 (m, 2H), 1.50-1.65 (m, 4H), 1.44 (s, 9H).

Workup

  1. customthe general hydrolysis procedure
  2. customwere reacted

Sources & evidence

ORD record
ord-8209c4592f8b4578932d14aa2f8a135a
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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