Water → HCID 22730138, compound

HRID 2085748Notes

Reaction equation

HRID 2085748 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 (24 mg, 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) δ8.49 (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-40637ca5cec64e699621d7056d399c68
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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