Hydrochloric Acid → HCID 86746994, compound

HRID 1463931Notes

Reaction equation

HRID 1463931 reaction equation
[F:1][C:2]([F:34])([CH2:31][CH2:32][CH3:33])[CH:3]([OH:30])[CH2:4][CH2:5][CH2:6][C@H:7]1[C@H:11]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH2:10][C@H:9]([OH:19])[C@@H:8]1[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].C(N(CC)CC)C.Cl>C(Cl)Cl>[F:34][C:2]([F:1])([CH2:31][CH2:32][CH3:33])[C:3](=[O:30])[CH2:4][CH2:5][CH2:6][C@H:7]1[C@H:11]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH2:10][C:9](=[O:19])[C@@H:8]1[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 86746995HCID 86746995, compound

Product 1

HCID 86746994HCID 86746994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the above solution was added a solution of methyl (Z)-7-[(1 R)-(2 R,3 R,5 S)-2-{5,5-difluoro-4(RS)-hydroxy-octyl}-5-hydroxy-3-tetra-hydropyranyloxycyclopentyl]hept- 5-enoate (18) (0.244 g) in methylene chloride. The resultant mixture was warmed to -25° C. and stirred for 1 hour. Triethylamine (0.60 ml) was added thereto and the reaction mixture was stirred for additional 30 minutes, poured into 1N hydrochloric acid, and then worked up with the conventional procedure. The obtained product was subjected to silicagel column chromatography to give the titled compound (19).

Workup

  1. stirringthe reaction mixture was stirred for additional 30 minutes

Sources & evidence

ORD record
ord-be939a6c9d9e480fa69d0de1450dbbea
Source dataset
uspto-grants-1994_04
Patent number
US05302617

Reaction notes

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