Sodium Acetate → 4-N-(Carbomethoxymethyl)-6-(carboethoxy-3-phenylpropylamino)-perhydro-1,4-thiazepin-5-one

HRID 1981891Notes

Reaction equation

HRID 1981891 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[NH2:8][CH:9]1[CH2:15][S:14][CH2:13][CH2:12][N:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:10]1=[O:21].[C:22]([O-])(=O)[CH3:23].[Na+].O=[C:28]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)C(OCC)=O.C([BH3-])#N.[Na+]>CO>[C:17]([CH2:16][N:11]1[C:10](=[O:21])[CH:9]([N:8]([C:3]([O:5][CH2:22][CH3:23])=[O:4])[CH2:28][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:15][S:14][CH2:13][CH2:12]1)([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 136337346-Amino-4-N-(carbomethoxymethyl)-perhydro-1,4-thiazepin-5-one, Trifluoroacetate Salt

Product 1

HCID 233180554-N-(Carbomethoxymethyl)-6-(carboethoxy-3-phenylpropylamino)-perhydro-1,4-thiazepin-5-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6-Amino-4-N-(carbomethoxymethyl)perhydro-1,4-thiazepin-5-one, trifluoroacetate salt (0.166 g), sodium acetate (0.04 g), and ethyl 2-keto-4-phenylbutyrate are dissolved in 1 ml of methanol. After 1/2 hour at room temperature, a solution of sodium cyanoborohydride (0.16 g) in 0.5 ml of methanol is added dropwise over a period of one hour. At the end of seven hours, the reaction mixture is partitioned between chloroform and water. The aqueous phase is adjusted to pH 10 with sodium bicarbonate. The organic layer is separated and washed two more times with water. After chromatography on silica gel (1:1 ethyl acetate-hexanes), the product is obtained as an oil (0.17 g). The NMR spectrum shows a singlet at 7.2, complex absorption between 3.7 and 4.4, a multiplet between 3.1 and 3.4, a multiplet between 3.6 and 3.9, a multipet between 1.9 and 2.2, and a triplet at 1.3.

Workup

  1. customAt the end of seven hours, the reaction mixture is partitioned between chloroform and water
  2. customThe organic layer is separated
  3. washwashed two more times with water

Sources & evidence

ORD record
ord-96d442a62f96407f978cde1beddc0b11
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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