Sodium borohydride → HCID 51347903, compound

HRID 244517Notes

Reaction equation

HRID 244517 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C@:20]4([S:39][CH3:40])[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:38])[CH:27]5[CH2:32][CH2:31][N:30]([C:33]6[S:34][CH:35]=[CH:36][N:37]=6)[CH2:29][CH2:28]5)[CH2:21]4)=[O:19])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[OH:38][CH:26]([CH:27]1[CH2:28][CH2:29][N:30]([C:33]2[S:34][CH:35]=[CH:36][N:37]=2)[CH2:31][CH2:32]1)[CH2:25][N:22]1[CH2:23][CH2:24][C@@:20]([S:39][CH3:40])([C:18]([NH:17][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][N:9]=[C:8]3[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[O:19])[CH2:21]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 51030061HCID 51030061, compound

Product 1

HCID 51347903HCID 51347903, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7 (17 mg, 0.03 mmol) (Example 1) in MeOH (3 mL) was added NaBH4 (20 mg, 0.5 mmol). The mixture was stirred at room temperature for 3 hrs before it was concentrated to dryness. The residue was purified on a prep TLC plate eluting with 10% ammonia /MeOH (2 M) in CH2Cl2 to yield a yellow solid 31 (10 mg, 59%). LCMS M+1=578.3 retention time=1.70 min.

Workup

  1. concentrationwas concentrated to dryness
  2. customThe residue was purified on a prep TLC plate
  3. washeluting with 10% ammonia /MeOH (2 M) in CH2Cl2

Sources & evidence

ORD record
ord-ec2613c5b4ec457b80f5370c35a37b50
Source dataset
uspto-grants-2014_02
Patent number
US08658651B2

Reaction notes

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