Acetic Acid → HCID 21070326, compound

HRID 1371543Notes

Reaction equation

HRID 1371543 reaction equation
CC(O)=O.Cl.[CH3:6][NH:7][CH3:8].[CH:9]([C:11]1[CH:50]=[CH:49][C:14]([CH2:15][CH:16]([NH:24][C:25](=[O:48])[CH2:26][CH:27]([NH:34][S:35]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)(=[O:37])=[O:36])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17](=[O:23])[N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:6][N:7]([CH2:9][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][CH:16]([NH:24][C:25](=[O:48])[CH2:26][CH:27]([NH:34][S:35]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=2)(=[O:36])=[O:37])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:17](=[O:23])[N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:49][CH:50]=1)[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10473Dimethylamine, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 21070329HCID 21070329, compound

Product 1

HCID 21070326HCID 21070326, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1 ml of AcOH and 0.129 g of dimethylamine hydrochloride are added to a solution of 0.830 g of the compound obtained in step A of Example 17 in 10 ml of DCM, followed by portionwise addition of 0.456 g of sodium triacetoxyborohydride, and the mixture is stirred for 18 hours at RT. The reaction mixture is diluted with DCM, the organic phase is washed with saturated NaCl solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a chloroform/MeOH mixture (95/5; v/v). 0.52 g of the expected product is obtained.

Workup

  1. washthe organic phase is washed with saturated NaCl solution
  2. dry with materialdried over Na2SO4
  3. customthe solvent is evaporated off under vacuum
  4. customThe residue is chromatographed on silica gel
  5. washeluting with a chloroform/MeOH mixture (95/5; v/v)

Sources & evidence

ORD record
ord-587b495aff5748e98af1191e1df8f750
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

Loading…