Hydrochloric Acid → HCID 59300623, compound

HRID 1675282Notes

Reaction equation

HRID 1675282 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]([C:26]3[CH:30]=[C:29]([CH3:31])[O:28][N:27]=3)[CH2:21][C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C1COCC1.CO>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C@@H:20]([C:26]3[CH:30]=[C:29]([CH3:31])[O:28][N:27]=3)[CH2:21][C:22]([OH:24])=[O:23])=[CH:18][CH:19]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59300689HCID 59300689, compound

Product 1

HCID 59300623HCID 59300623, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 39.3 (25 mg) in THF/MeOH (1:1, 4 mL) was treated with 2N aqueous NaOH solution (0.2 mL) and stirred for 2 hours at room temperature. The reaction mixture was acidified with aqueous 3N HCl while cooled with ice-water, and extracted with EtOAc to obtain 39, which was chromatographed on a silica gel column, eluting with 5˜10% MeOH in DCM. MS ESI (neg.) m/e: 480.1 (M−H). 1HNMR (CDCl3) δ 7.13 (s, 1H), 7.04 (d, 2H, J=7.27Hz), 7.01-6.98 (m, 2H), 6.80 (s, 1H), 6.69 (d, 2H, J=Hz, J=8.62Hz), 6.46 (d, 2H, J=8.61Hz), 4.99 (s, 1H), 4.59 (s, 2H), 3.95 (t, 1H, J=7.60Hz), 2.80 (m, 1H), 2.46 (m, 1H), 1.82 (s, 3H).

Workup

  1. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-eaa98281b3124ef69a6770dc4de49bf1
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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