Acetic Acid → HCID 67043932, compound

HRID 2040446Notes

Reaction equation

HRID 2040446 reaction equation
[C:1](O[BH3-])(=O)C.[Na+].[CH3:7][N:8]([CH3:49])[C:9]([C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]1[C:17]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][CH3:48])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=2)[N:19]([S:27]([C:30]2[CH:39]=[C:38]3[C:33]([CH2:34][CH2:35][NH:36][CH2:37]3)=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:18]1=[O:40])=[O:10].C(O)(=O)C.C=O>>[CH3:7][N:8]([CH3:49])[C:9]([C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]1[C:17]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][CH3:48])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=2)[N:19]([S:27]([C:30]2[CH:39]=[C:38]3[C:33]([CH2:34][CH2:35][N:36]([CH3:1])[CH2:37]3)=[CH:32][CH:31]=2)(=[O:28])=[O:29])[C:18]1=[O:40])=[O:10]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 67043937HCID 67043937, compound

Product 1

HCID 67043932HCID 67043932, compoundYield 65.2%

Procedure

Sodium acetoxyborohydride (0.36 mmol, 76.27 mg) was added to a solution of Example 61 (0.24 mmol, 0.15 g), acetic acid (0.24 mmol, 14.4 mg) and aq. formaldehyde (37%, 0.26 mmol, 21.42 mg). The mixture was stirred at RT for 12 h and evaporated in vacuo. The residue was solved in H2O and extracted with ethyl acetate. The organic phase was dried, filtrated and evaporated. The crude product was then purified on a column of silicagel eluted with 5% MeOH in CH2Cl2 to afford 100 mg of the required product.

Workup

  1. customevaporated in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. filtrationfiltrated
  5. customevaporated
  6. customThe crude product was then purified on a column
  7. washof silicagel eluted with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-15f0d633910c4721a5af55c41b1b4f11
Source dataset
uspto-grants-2013_11
Patent number
US08580842B2

Reaction notes

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