Ethanol → HCID 58497730, compound

HRID 1616684Notes

Reaction equation

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

Participants

Reactant 3

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 58497663HCID 58497663, compound

Product 1

HCID 58497730HCID 58497730, compound

Conditions

Temperature: -20 °C

Procedure

SOCl2 (5 mL) is added dropwise to a suspension of 4-[(2R,6S)-10-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carbonyl]-cyclohexanecarboxylic acid (100 mg) in ethanol (5 mL) cooled to −20° C. Then, the cooling bath is removed and the resulting mixture is stirred at ambient temperature overnight. The solution is concentrated under reduced pressure and the residue is triturated with acetone and dried.

Workup

customThen, the cooling bath is removed
concentrationThe solution is concentrated under reduced pressure
customthe residue is triturated with acetone
customdried

Sources & evidence

ORD record: ord-3ed3d32d85884f29a758a8ce0e37624d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765780B2

Reaction notes

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