Water → HCID 22730138, compound

HRID 2356081Notes

Reaction equation

HRID 2356081 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) 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-9bfdd3eb1c184f12979cc944b352bcf7
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

Loading…