Hydrochloric Acid → [5-(3-Amino-propoxy)-1,3-dihydro-isoindol-2-yl]-(2,4-dihydroxy-5-isopropyl-phenyl)-methanone hydrochloride

HRID 644642Notes

Reaction equation

HRID 644642 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][N:16]([C:21](=[O:33])[C:22]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[C:25]([OH:31])=[CH:24][C:23]=1[OH:32])[CH2:15]2)(C)(C)C.[ClH:35]>CCOC(C)=O>[ClH:35].[NH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][N:16]([C:21]([C:22]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[C:25]([OH:31])=[CH:24][C:23]=1[OH:32])=[O:33])[CH2:15]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11955638HCID 11955638, compound

Product 1

HCID 66672375[5-(3-Amino-propoxy)-1,3-dihydro-isoindol-2-yl]-(2,4-dihydroxy-5-isopropyl-phenyl)-methanone hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of {3-[2-(2,4-dihydroxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindol-5-yloxy]-propyl}-carbamic acid tert-butyl ester (Example 46) (1 g) in EtOAc (10 ml) was treated with a saturated solution of HCl in EtOAC (20 ml) then stirred at room temperature for 2 hours. The reaction mixture was evaporated and re-evaporated with ethanol (×3). The title compound was isolated as a cream foam (840 mg). 1H NMR (DMSO-d6) 10.05 (1H, br s), 9.60 (1H, s), 7.88 (3H, br s), 7.30-7.18 (1H, m), 7.05 (1H, s), 7.00-6.85 (2H, m), 6.42 (1H, s), 4.75 (2H, br s) 4.70 (2H, br s), 4.05 (2H, t), 3.10 (1H, m), 3.00-2.95 (2H, m), 2.00 (2H, tt), 1.15 (6H, d). MS: [M+H]+ 371.

Workup

  1. customThe reaction mixture was evaporated
  2. customre-evaporated with ethanol (×3)

Sources & evidence

ORD record
ord-4b9db8b45b5a4aae873b7de01877636e
Source dataset
uspto-grants-2010_04
Patent number
US07700625B2

Reaction notes

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