Hydrochloric Acid → HCID 20505488, compound

HRID 355226Notes

Reaction equation

HRID 355226 reaction equation
[CH3:1][NH:2][CH3:3].Cl.[Si:5]([N:12]1[C@@H:15]([S:16][C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([CH:36]=O)[C:13]1=[O:38])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[Si:5]([N:12]1[CH:15]([S:16][C:17]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]([CH2:36][N:2]([CH3:3])[CH3:1])[C:13]1=[O:38])([C:8]([CH3:10])([CH3:9])[CH3:11])([CH3:7])[CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86737792HCID 86737792, compound

Product 1

HCID 20505488HCID 20505488, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent4×

Procedure

To a solution of dimethylamine (18.5 ml of a 2N solution in methanol, 36.9 mmoles) in methanol (80 ml) was added a solution of hydrochloric acid in methanol (2.5 ml of a 5N solution in methanol) followed by trans 1-(t-butyldimethylsilyl)-3-formyl-4-tritylthio-2-azetidinone (3.0 g, 6.16 mmoles) and by sodium cyanoborohydride (0.27 g, 4.31 mmoles). The mixture was stirred at room temperature for 3.5 h, poured onto ice-hydrochloric acid (pH=2) and made basic with sodium hydroxide (1N NaOH, pH=9). The mixture was extracted with ether and the ether phase was washed with brine, dried and evaporated to give the title compound as a crude oil (3.0 g).

Workup

  1. additionpoured onto ice-hydrochloric acid (pH=2)
  2. extractionThe mixture was extracted with ether
  3. washthe ether phase was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-62e2cdb8d5c9420d9f104bd20112d500
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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