Sodium Bicarbonate → HCID 56623257, compound

HRID 1462496Notes

Reaction equation

HRID 1462496 reaction equation
[NH2:1][CH:2]1[CH2:7][S:6][C@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]([CH2:14][C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[C:3]1=[O:24].C(=O)(O)[O-].[Na+].[CH2:30]([O:32][C:33](=[O:44])[C:34](=O)[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:31].C([BH3-])#N.[Na+]>C(O)(C)C>[CH2:30]([O:32][C:33]([CH:34]([NH:1][CH:2]1[CH2:7][S:6][C@H:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:4]([CH2:14][C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])=[O:16])[C:3]1=[O:24])[CH2:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:44])[CH3:31]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 56624470HCID 56624470, compound

Product 1

HCID 56623257HCID 56623257, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Procedure

A solution of (R)-dihydro-5-amino-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, 2-(trimethylsilyl)ethyl ester (9 mmole) in dry isopropanol (12 ml.) under nitrogen is treated with sodium bicarbonate (2.25 mmole) followed by ethyl-2-oxo-4-phenylbutyrate (9.3 g., 45 mmole) dissolved in isopropanol (8 ml.). To the resulting suspension is added powdered 3 A° molecular sieves (8 g.). The reaction mixture is stirred for one hour while the pH is maintained at around 7.0. Next a solution of sodium cyanoborohydride (1.13 g., 18 mmole) in isopropanol (14 ml.) is added incrementally over a 5 hour period while continuing to maintain neutral pH. The reaction mixture is then stirred overnight at room temperature, then filtered (celite), concentrated in vacuo, and partitioned between ether and water. Normal work up of the organic extract followed by column chromatography on silica gel yields (R)-dihydro-5-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, 2-(trimethylsilyl)ethyl ester as a mixture of diastereomers.

Workup

  1. additionTo the resulting suspension is added
  2. temperatureis maintained at around 7.0
  3. temperatureto maintain neutral pH
  4. stirringThe reaction mixture is then stirred overnight at room temperature
  5. filtrationfiltered (celite)
  6. concentrationconcentrated in vacuo
  7. custompartitioned between ether and water
  8. extractionNormal work up of the organic extract

Sources & evidence

ORD record
ord-2429af5661514c14ba731c99d3bda23a
Source dataset
uspto-grants-1984_07
Patent number
US04460579

Reaction notes

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