Acetic Acid → HCID 23318045, compound

HRID 1981894Notes

Reaction equation

HRID 1981894 reaction equation
[NH2:1][CH:2]1[CH2:8][S:7][CH2:6][CH2:5][N:4]([CH:9]([C:11]([OH:13])=[O:12])[CH3:10])[C:3]1=[O:14].O=[C:16]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:11]([CH:9]([N:4]1[C:3](=[O:14])[CH:2]([NH:1][CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:8][S:7][CH2:6][CH2:5]1)[CH3:10])([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 23318049HCID 23318049, compound

Product 1

HCID 23318045HCID 23318045, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Amino-4-N-(1-carboxyethyl)perhydro-1,4-thiazepin-5-one (0.05 g) is suspended in 1 ml of methanol. Ethyl 2-keto-4-phenylbutyrate (0.24 g) and acetic acid (0.02 g) are added. A 1M solution of sodium cyanoborohydride (0.75 ml) is added dropwise over a period of twenty hours. After removal of methanol, the reaction mixture is taken up in water and loaded onto a column of Dowex-50 (on the proton cycle). After thorough washing with water, the column is developed with 5% pyridine solution. Lyophilization of the eluent afforded the crude product (0.08 g), which is purified by preparative thin layer chromatography on silica gel (9:1 chloroform-methanol containing 5% formic acid). The product is obtained as an oil (0.07 g). The NMR spectrum is consistent with the assigned structure.

Workup

  1. customAfter removal of methanol
  2. washAfter thorough washing with water
  3. customLyophilization of the eluent afforded the crude product (0.08 g), which
  4. customis purified by preparative thin layer chromatography on silica gel (9:1 chloroform-methanol containing 5% formic acid)

Sources & evidence

ORD record
ord-5a39e1cdfdd644b7bbb1b40507e4cbbe
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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