Water → HCID 22730138, compound

HRID 1785808Notes

Reaction equation

HRID 1785808 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:20]([NH:23][C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][CH:34]([CH2:37][CH2:38][CH:39]=[O:40])[CH2:33][CH2:32]3)=[CH:27][CH:26]=2)(=[O:22])=[O:21])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:3])=[O:2].[BH4-].[Na+].O>CO.ClCCl>[OH:40][CH2:39][CH2:38][CH2:37][CH:34]1[CH2:33][CH2:32][N:31]([C:28]2[CH:27]=[CH:26][C:25]([C:24]([NH:23][S:20]([C:6]3[CH:7]=[CH:8][C:9]([NH:10][CH2:11][CH2:12][S:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)(=[O:21])=[O:22])=[O:41])=[CH:30][CH:29]=2)[CH2:36][CH2:35]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22730844HCID 22730844, compound

Product 1

HCID 22730138HCID 22730138, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 226 (15 mg, 0.025 mmol) in methanol (0.5 mL) and dichloromethane (2 drops) at 0° C. was treated with NaBH4 (24mg, 0.6 mmol), stirred for 1 hour, warmed to room temperature, and stirred for 90 minutes. The mixture was treated with water and filtered. The filter cake was treated with dichloromethane (5 mL) and methanol (1 drop), stirred for 2 hours, and filtered. The filter cake was washed with diethyl ether, and dried under vacuum to provide the desired product. MS(ESI(−)) m/e 597 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.49 (d, 1H), 8.45 (d, 1H), 7.85 (dd, 1H), 7.71 (d, 2H), 7.40 (m, 2H), 7.30 (m, 2H), 7.20 (m, 2H), 6.95 (d, 1H), 6.90 (d, 2H), 4.34 (t, 1H), 3.75 (m, 2H), 3.60 (m, 2H), 3.39 (m, 2H), 3.25 (m, 2H), 2.65 (m, 2H), 1.71 (m, 2H), 1.45 (m, 2H), 1.25-1.11 (m, 4H).

Workup

  1. stirringstirred for 90 minutes
  2. filtrationfiltered
  3. additionThe filter cake was treated with dichloromethane (5 mL) and methanol (1 drop)
  4. stirringstirred for 2 hours
  5. filtrationfiltered
  6. washThe filter cake was washed with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-50a10d99e6b849369f1b7639f16475a6
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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