Ethanol → HCID 86739554, compound

HRID 1462492Notes

Reaction equation

HRID 1462492 reaction equation
[C:1]1(=[O:23])[N:5]([CH:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][PH:8](=[O:10])[OH:9])[C:4](=[O:18])[C:3]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:2]12.P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:30](O)[CH3:31].C(N(CC)CC)C.[NH2:40][CH:41]1[CH2:46][S:45][C@H:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:43]([CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55])[C:42]1=[O:59]>C1C=CC=CC=1.C(Cl)Cl>[C:4]1(=[O:18])[N:5]([CH:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][P:8]([NH:40][CH:41]2[CH2:46][S:45][C@H:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[N:43]([CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55])[C:42]2=[O:59])([O:9][CH2:30][CH3:31])=[O:10])[C:1](=[O:23])[C:2]2=[CH:22][CH:21]=[CH:20][CH:19]=[C:3]12

Participants

8

Reactant 5

HCID 702EthanolHCID 8471Triethylamine2×HCID 24819Phosphorus pentachlorideHCID 86739548HCID 86739548, compoundHCID 178514982HCID 178514982, compound

Product 1

HCID 86739554HCID 86739554, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of (2-phthalimido-3-phenylpropyl)phosphinic acid in dry benzene is treated with phosphorus pentachloride and stirred at room temperature under argon for an hour. The mixture is then refluxed for 15 minutes, cooled and evaporated to dryness at room temperature (0.5 mm. of Hg). The residue is taken up in dry methylene chloride and reacted successively with a mixture of ethanol (1 eq.) and triethylamine (1 eq.) in methylene chloride and (R)-dihydro-5-amino-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, ethyl ester in the presence of triethylamine according to the procedure of Example 1(f). Work up of the reaction mixture according to the procedure of Example 1(f) yields (R)-dihydro-5-[[[2-phthalimido-3-phenylpropyl]ethoxyphosphinyl]amino]-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, ethyl ester.

Workup

  1. temperatureThe mixture is then refluxed for 15 minutes
  2. temperaturecooled
  3. customevaporated to dryness at room temperature (0.5 mm. of Hg)

Sources & evidence

ORD record
ord-127b3033eed844b581a48da0a84f1881
Source dataset
uspto-grants-1984_07
Patent number
US04460579

Reaction notes

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