Hydrochloric Acid → HCID 22120819, compound

HRID 1274226Notes

Reaction equation

HRID 1274226 reaction equation
O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].C([O:15][C:16](=[O:47])[CH:17]([C:35]1[S:36][C:37]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:38][CH:39]=1)[NH:18][C:19](=[O:34])[CH:20]([CH2:29][S:30]C(=O)C)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C.Cl>O.CO>[CH2:40]([C:37]1[S:36][C:35]([CH:17]([C:16]([OH:47])=[O:15])[NH:18][C:19](=[O:34])[CH:20]([CH2:29][SH:30])[CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:39][CH:38]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73972Sodium sulfide nonahydrateHCID 22120796HCID 22120796, compound

Product 1

HCID 22120819HCID 22120819, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium sulphide nonahydrate (464 mg) in water (3 ml) was added to a stirred solution of 2-[(5-benzyl)thien-2-yl]-N-[2-(acetylthiomethyl)-4-phenylbutyryl]glycine ethyl ester (Description 40) (330 mg) in methanol (3 ml) under argon. Further portions of methanol (totalling 5 ml) were added over 45 min. The mixture was stirred for a further 20 min. and then dilute hydrochloric acid (2 ml) was added and the mixture partitioned between ethyl acetate and water. The organic phase was washed with water and brined, dried over magnesium sulphate and evaporated. The product (209 mg) was isolated by column chromatography of the residue using gradient elution (Kieselgel:5% going to 10% methanol in chloroform). vmax (CHCl3) 3423, 3295, 1723 and 1674 cm-1. δ (CD3SOCD3) 1.70-1.90 (2H, m), 2.43-2.70 (5H, m), 4.07 and 4.09 (2H, two s's), 5.43 (1H, d, J 7.77 Hz), 6.73-6.75 (1H, m), 6.88 and 6.91 (1H, two d's, J 3.42 Hz), 7.09-7.35 (10H, m). m/z 439 (M+). [Found (HRMS): m/z 439.1281. Calc. for C24H25NO3S2 : 439.1276].

Workup

  1. customthe mixture partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-2f54c52b039143fa93bc423d4e5417d9
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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