Acetic Acid → HCID 67407693, compound

HRID 1174272Notes

Reaction equation

HRID 1174272 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:32])[N:17]([CH2:21][C:22]3[N:26]([CH3:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[N:23]=3)[CH2:18]C=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH3-][C:34]#[N:35].[Na+].[C:37]([OH:40])(=[O:39])[CH3:38]>CO>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:17]([CH2:21][C:22]3[N:26]([CH3:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[N:23]=3)[CH2:18][CH2:34][NH:35][C@@H:38]([C@@H:8]([CH3:7])[CH2:9][CH3:10])[C:37]([O:40][C:5]([CH3:6])([CH3:13])[CH3:4])=[O:39])=[O:32])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 72942063HCID 72942063, compound

Product 1

HCID 67407693HCID 67407693, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 59C (0.81 mmol ) and (L)-methyl iso-leucinate hydrochloride (0.182 g, 0.813 mmol) in methanol (3.2 mL) and acetic acid (0.032 mL) was treated with NaCNBH3 (0.104 g, 1.65 mmol), stirred at 25° C. for 1 hour, and partitioned between water and dichloromethane. The organic phase layer was separated and washed with 1N NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The crude product was used without further purification.

Workup

  1. custompartitioned between water and dichloromethane
  2. customThe organic phase layer was separated
  3. washwashed with 1N NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-ed1d25cfc9414ae3a5a9f9b2af6e2119
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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