Acetic Acid → HCID 10004563, compound

HRID 1294744Notes

Reaction equation

HRID 1294744 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=2)[N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[C:35]1(=O)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[C:42](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH:35]1([N:1]([CH3:42])[C:2]2[CH:3]=[C:4]([C@@H:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[C:22]3[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=3)[CH:5]=[CH:6][CH:7]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 11590834HCID 11590834, compound

Product 1

HCID 10004563HCID 10004563, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a room temperature solution of INTERMEDIATE 5a (300 mg; 0.64 mmol) in 1,2-dichloroethane (15 mL) were added cyclohexanone (0.20 mL; 1.93 mmol), sodium triacetoxy borohydride (0.43 g; 2.05 mmol) and acetic acid (37 μL; 0.64 mmol). The reaction mixture was stirred for 6 hours then was washed with two portions of saturated sodium bicarbonate. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography eluting with 4% methanol in dichloromethane gave the desired product.

Workup

  1. washthen was washed with two portions of saturated sodium bicarbonate
  2. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washColumn chromatography eluting with 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-faff19b1a59c4b7397003b4f097ea86c
Source dataset
uspto-grants-2007_07
Patent number
US07241764B2

Reaction notes

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