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

HRID 1981891
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HRID 1981891 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887
Methanol
용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96d442a62f96407f978cde1beddc0b11
출처 데이터셋
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04594341

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