Water → Carbonic acid 3-(4-chloro-2,6-dimethyl-phenyl)-1-ethoxycarbonyloxy-8-methoxy-2-oxo-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester

HRID 1473787Notes

Reaction equation

HRID 1473787 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:23])[N:11]([OH:22])[C:12]3([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]3)[C:13]=2[OH:14])=[C:4]([CH3:24])[CH:3]=1.C(N(CC)CC)C.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34].[OH2:38].C1[CH2:43][O:42][CH2:41][CH2:40]1>>[CH2:41]([O:42][C:43](=[O:38])[O:14][C:13]1[C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[N:11]([O:22][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:10](=[O:23])[C:9]=1[C:5]1[C:6]([CH3:8])=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH3:24])[CH3:40]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 584279803-(4-Chloro-2,6-dimethyl-phenyl)-1,4-dihydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one

Product 1

HCID 58428109Carbonic acid 3-(4-chloro-2,6-dimethyl-phenyl)-1-ethoxycarbonyloxy-8-methoxy-2-oxo-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-chloro-2,6-dimethyl-phenyl)-1,4-dihydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (140 mg, 0.40 mmol) and triethylamine (0.1 ml, 72 mg, 0.71 mmol) in THF (3 ml) at 0° C. was added a solution of ethyl chloroformate (0.05 ml, 52 mg, 0.48 mmol) dissolved in THF (2 ml) dropwise. The suspension was stirred at 0° C. for 30 minutes. Then the reaction mixture was poured into cold (0° C.) water and thoroughly extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The raw material was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:4). Yield: 70 mg of carbonic acid 3-(4-chloro-2,6-dimethyl-phenyl)-1-ethoxycarbonyloxy-8-methoxy-2-oxo-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester (title compound P1ii.115) as a colorless gum.

Workup

  1. extractionthoroughly extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe raw material was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:4)

Sources & evidence

ORD record
ord-523afe0c55654f4eb83e185c8709f51c
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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