Hydrochloric Acid → HCID 67496615, compound

HRID 1022478Notes

Reaction equation

HRID 1022478 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:5].[S:30]1[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(O)(=O)C>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:2]([NH:1][CH:33]2[CH2:34][CH2:35][S:30][CH2:31][CH2:32]2)=[C:3]([CH:18]=1)[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:5])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 66173Tetrahydrothiopyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 67496543HCID 67496543, compound

Product 1

HCID 67496615HCID 67496615, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.235 g of 2-amino-5-(benzyloxy)-N-(3,4-dimethoxybenzyl)benzamide, 0.090 g of tetrahydro-4H-thiopyran-4-one and 0.78 g of sodium triacetoxyborohydride in 0.5 ml of acetic acid is irradiated in a microwave field for 5 minutes at 130° C. 1N HCl is added and the mixture is extracted with EtOAc. The organic phase is dried over MgSO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a heptane/EtOAc mixture from (90/10, v/v) to (20/80, v/v) to give 0.2 g of the expected product.

Workup

  1. customis irradiated in a microwave field for 5 minutes at 130° C
  2. extractionthe mixture is extracted with EtOAc
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe filtrate is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluting with a heptane/EtOAc mixture from (90/10

Sources & evidence

ORD record
ord-491d6a31f57e44318b442c6565f32888
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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