Sodium borohydride → HCID 71237843, compound

HRID 1409680Notes

Reaction equation

HRID 1409680 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C@@H:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:21])[CH2:15][C@H:14]3[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C@@H:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[OH:21])[CH2:15][C@H:14]3[C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71237789HCID 71237789, compound

Product 1

HCID 71237843HCID 71237843, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from step A (40 mg, 0.084 mmol) in ethanol (1.0 ml) was treated at rt with sodium borohydride (31.9 mg, 0.844 mmol). The mixture was stirred at rt for 16 h, then quenched with 2M aq NaOH (0.1 mL) and concentrated. Direct purification of the residue by RP-HPLC(C18, acetonitrile, water, 0.1% TFA) afforded the title compound. HPLC/MS: 476.3, 478.3 (M+1); Rt=1.66 min (LC-4 HPLC conditions).

Workup

  1. customquenched with 2M aq NaOH (0.1 mL)
  2. concentrationconcentrated
  3. customDirect purification of the residue by RP-HPLC(C18, acetonitrile, water, 0.1% TFA)

Sources & evidence

ORD record
ord-edb418e8be04407d8d9eb634a491e2fe
Source dataset
uspto-grants-2014_12
Patent number
US08921394B2

Reaction notes

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