Water → HCID 15381474, compound

HRID 2258117Notes

Reaction equation

HRID 2258117 reaction equation
Cl.[SH:2][CH:3]1[CH2:6][N:5]([C:7]2[S:8][CH2:9][CH2:10][N:11]=2)[CH2:4]1.O.C1(P(O[C:28]2[C@H:29]([CH3:52])[C@@H:30]3[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:31]3[C:32]=2[C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=2)=[O:34])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)CC)(C)C>C(OC(=O)C)C.C(Cl)(Cl)Cl.C(#N)C>[S:8]1[CH2:9][CH2:10][N:11]=[C:7]1[N:5]1[CH2:6][CH:3]([S:2][C:28]2[C@H:29]([CH3:52])[C@@H:30]3[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:31]3[C:32]=2[C:33]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][C:40]([N+:43]([O-:45])=[O:44])=[CH:41][CH:42]=2)=[O:34])[CH2:4]1

Participants

8

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 119748831-(4,5-Dihydro-1,3-thiazol-2-yl)azetidine-3-thiol--hydrogen chloride (1/1)HCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate

Product 1

HCID 15381474HCID 15381474, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

There was dissolved 700 mg of 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine hydrochloride (8), which was obtained in the above Example 6, in 15 ml of a mixed solvent composed of water, acetonitrile and chloroform, and, to the resulting solution, there was added 1668 mg of p-nitrobenzyl (1R,5R,6S)-2-(diphenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate (14). To the obtained solution which was being cooled with ice, there was added 2.8 ml of diisopropylethylamine in the stream nitrogen, and the resulting mixture was stirred at the same temperature for two hours. To the reaction liquid, there was added ethylacetate, and the resulting solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, and, then, the solvent was evaporated in a vacuum, and the obtained residue was subjected to silica gel column chromatography (eluent: chloroform-acetone), and, thus, there was produced 1339 mg (yield: 92%) of p-nitrobenzyl (1R,5S,6S)-2-[1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate (15).

Workup

  1. temperatureTo the obtained solution which was being cooled with ice, there
  2. customTo the reaction liquid, there
  3. washthe resulting solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride
  4. customthe solvent was evaporated in a vacuum

Sources & evidence

ORD record
ord-f9738477d84846a59c3d7f7e99d1ad22
Source dataset
uspto-grants-1997_08
Patent number
US05659043

Reaction notes

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