Hydrochloric Acid → N-[4-(5-carboxypentylcarbamoyl)-cyclohexylmethyl]-2-(methylcarbamoyl)-ethylthiosuccinimide

HRID 1836166

반응식

HRID 1836166 반응식
[CH3:1][NH:2][C:3](=[O:9])[CH2:4][CH2:5][C:6](=[S:8])C.[OH-].[K+].Cl.[N+]([C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=O)([S-])=S.C1C(SSC2C=CC([N+]([O-])=O)=C(C(O)=O)C=2)=CC(C(O)=O)=C([N+]([O-])=O)C=1.[CH2:51]1[CH:56]([CH2:57][N:58]2C(=O)C=CC2=O)CC[CH:53]([C:65]([O:67]N2C(=O)CCC2=O)=[O:66])[CH2:52]1.C([O-])(=O)CCCCC.[CH3:83][NH:84][C:85](=[O:89])[CH2:86][CH2:87]S>CO.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[C:65]([CH2:53][CH2:52][CH2:51][CH2:56][CH2:57][NH:58][C:18]([CH:17]1[CH2:16][CH2:24][CH:23]([CH2:1][N:2]2[C:3](=[O:9])[CH2:4][CH:5]([CH2:87][CH2:86][C:85](=[O:89])[NH:84][CH3:83])[C:6]2=[S:8])[CH2:22][CH2:21]1)=[O:20])([OH:67])=[O:66]

참가 물질

10

반응물 7

HCID 313Hydrochloric AcidHCID 62545,5'-Dithiobis(2-nitrobenzoic Acid)HCID 14797Potassium HydroxideHCID 6429063-Mercapto-N-methylpropanamideHCID 21865436(2-Carboxyphenyl)-sulfanylidene-sulfidoazaniumHCID 54417257N-methyl-(3-thioacetyl)propionamideHCID 131719433SMCC caproate

생성물 1

HCID 88051188N-[4-(5-carboxypentylcarbamoyl)-cyclohexylmethyl]-2-(methylcarbamoyl)-ethylthiosuccinimide

시약·촉매·용매 2

HCID 887Methanol용매HCID 62657Potassium Phosphate, Tribasic용매2회

실험 절차

The thiol ester of N-methyl-(3-thioacetyl)-propionamide (4.6 mg, 3.1×10−5 mol, see Example 3) was hydrolyzed by the addition of 0.62 ml of 0.12 M KOH in 80% methanol. After 10 min, 0.3 ml of 0.5 M potassium phosphate, pH 7 was added to the thiol compound and the pH adjusted to 7.5 with 1 N hydrochloric acid. The thiol concentration was 34 mM (determined by reaction with dithionitrobenzoic acid, DTNB). SMCC-caproate (8.7 mg, 2.5×10−5 mol) was dissolved in 0.4 ml of 0.5 M potassiumphosphate, pH 7.0, and the N-methyl-(3-mercapto)-propionamide solution (0.742 ml, 2.5×10−5 mol) added. The solution was gassed with argon and the tube sealed. After 12 hr at room temperature, no thiol remained and the solvent was removed in vacuo. The residue was dissolved in 0.117 ml water to make a 213 mM solution of the desired compound (see FIG. 1D).

후처리

  1. customthe tube sealed
  2. waitAfter 12 hr at room temperature
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in 0.117 ml water

출처 및 근거

ORD 기록
ord-03303f29abf44019829da393b7faea3b
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777190B1

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