Hydrochloric Acid → (5S,8S)-methyl-3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate

HRID 2038562

Reaction equation

HRID 2038562 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][C@@:12]3([CH2:17][C@@H:16]([C:18]([O:20][C:21](C)(C)C)=[O:19])[N:15](C(OC(C)(C)C)=O)[CH2:14]3)[O:11][C:10]2=[O:32])[CH:6]=[CH:7][CH:8]=1>CO>[CH3:21][O:20][C:18]([C@@H:16]1[CH2:17][C@:12]2([O:11][C:10](=[O:32])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=3)[CH2:13]2)[CH2:14][NH:15]1)=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59547291(5S,8S)-di-tert-butyl 3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylate

Product 1

HCID 59547337(5S,8S)-methyl-3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylateYield 81.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Saturated HCl in MeOH (5 mL) was added to (5S,8S)-di-tert-butyl 3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylate (107 mg, 0.236 mmol) and stirred at room temp. overnight. The solution was concentrated and chromatography using DCM and 20% MeOH in DCM gave 60 mg (0.193 mmol) of (5S,8S)-methyl-3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (B3). 1H NMR (300 MHz, DMSO) 7.68 (s, 1H), 7.6-7.4 (m, 2H), 7.23 (m, 1H), 4.62 (m, 1H), 4.22 (m, 2H), 3.85-3.68 (m, 4H), 3.6-3.5 (m, 1H), 2.9-2.7 (m, 2H). LC MS+: 311.14 at 1.65 min (10-90%, 3-5 min, Formic Acid).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-61101c8219574b40962f4222cd2d4650
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Linked notes

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