Sodium sulfide nonahydrate → HCID 22120870, compound

HRID 1274234Notes

Reaction equation

HRID 1274234 reaction equation
O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].C([O:15][C:16](=[O:54])[CH:17]([C:35]1[S:36][C:37]([CH2:40][N:41]2[C:45]([C:46]([O:48]C)=[O:47])=[C:44]([C:50]([O:52]C)=[O:51])[N:43]=[N: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>O.CO>[C:50]([C:44]1[N:43]=[N:42][N:41]([CH2:40][C:37]2[S:36][C:35]([CH:17]([C:16]([OH:54])=[O:15])[NH:18][C:19](=[O:34])[CH:20]([CH2:29][SH:30])[CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:39][CH:38]=2)[C:45]=1[C:46]([OH:48])=[O:47])([OH:52])=[O:51]

Participants

5

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 22120831HCID 22120831, compound

Product 1

HCID 22120870HCID 22120870, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium sulphide nonahydrate (1.09 g) in water (6 ml) was added to a stirred solution of 2-[5-{4,5-di(methoxycarbonyl)triazol-1-ylmethyl}thien-2-yl]-N-[2-(acetylthiomethyl)-4-phenylbutyryl]glycine ethyl ester (Description 71) (400 mg) in methanol (6 ml). The mixture partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The residue was crystallised by trituration with ether and ethyl acetate, and the solid filtered off and washed with ether then dried under vacuum to give the title compound (92 mg). vmax (nujol) 3294, 1732, 1643 cm-1. m/z (M-H-).

Workup

  1. customThe mixture partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was crystallised by trituration with ether and ethyl acetate
  6. filtrationthe solid filtered off
  7. washwashed with ether
  8. customthen dried under vacuum

Sources & evidence

ORD record
ord-97b29f0d07f246b6a530a7e97cc877c2
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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