S-(3-Chloro-2-methyl-3-oxopropyl) (S)-ethanethioate → Benzyl 3-(3-acetylthio-2-(S)-methyl-1-oxopropyl)-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-carboxylate

HRID 1651455Notes

Reaction equation

HRID 1651455 reaction equation
[C:1]([S:4][CH2:5][C@H:6]([CH3:10])[C:7](Cl)=[O:8])(=[O:3])[CH3:2].C(OC([C@@H](N[C@H](C([N:30]1[N:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[S:32][C@H:31]1[C:41]([OH:43])=[O:42])=O)C)CCC1C=CC=CC=1)=O)C>ClCCl>[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7]([N:30]1[N:34]=[C:33]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[S:32][CH:31]1[C:41]([O:43][CH2:33][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:42])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10954137S-(3-Chloro-2-methyl-3-oxopropyl) (S)-ethanethioate2×HCID 137732543-[N-(1-(S)-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(S)-carboxylic acid

Product 1

HCID 13773289Benzyl 3-(3-acetylthio-2-(S)-methyl-1-oxopropyl)-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Acetylthio-2-(S)-methylpropanoyl chloride (2.3 g) in dichloromethane (30 ml) was added over 5 minutes to a stirred mixture of the product of Example 1, step a) (3.6 g) and polyvinylpyridine (2.4 g) in dichloromethane (60 ml). The mixture was stirred at room temperature for 20 hours and 3-acetylthio-2-(S)-methylpropanoyl chloride (1.2 g) was then added. The mixture was stirred for a further 2 hours, filtered and the filtrate stirred with a saturated solution of sodium bicarbonate for 1 hour. The organic phase was separated, washed with water, dried and evaporated to a gum. The residue was purified by flash chromatography to give the sub-title product (4.4 g) as an oil.

Workup

  1. stirringThe mixture was stirred for a further 2 hours
  2. filtrationfiltered
  3. stirringthe filtrate stirred with a saturated solution of sodium bicarbonate for 1 hour
  4. customThe organic phase was separated
  5. washwashed with water
  6. customdried
  7. customevaporated to a gum
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-aab7c6cd157f473e95a10e4432cae8a6
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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