Ammonia → HCID 23146899, compound

HRID 495295Notes

Reaction equation

HRID 495295 reaction equation
C(Cl)(=O)OC.C(N(CC)CC)C.[CH2:13]([C:15]1[C:20]([O:21]C(OC)=O)=[CH:19][C:18]([O:26]C(OC)=O)=[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)[C:16]=1[CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[CH3:14].[BH4-].[Na+].N>CO.O1CCCC1.O>[CH2:13]([C:15]1[C:20]([OH:21])=[CH:19][C:18]([OH:26])=[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)[C:16]=1[CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44])[CH3:14]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 23147180HCID 23147180, compound

Product 1

HCID 23146899HCID 23146899, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In the same manner as in Example 118, 1-{3-(3-hydroxyphenyl)-2-[2-(2-methoxyethoxy)ethyl]-4,6-bis(methoxycarbonyloxy)phenyl]ethanone was obtained from Compound 165 (320 mg, 0.92 mmol) obtained in Example 165, using methyl chlorocarbonate (0.2 mL, 2.6 mmol), triethylamine (0.4 mL, 2.9 mmol) and tetrahydrofuran (10 mL); and from the resulting compound, obtained was 4-ethyl-2-(3-hydroxyphenyl)-3-[2-(2-methoxyethoxy)ethyl]-1,5-bis(methoxycarbonyloxy)benzene, using sodium borohydride (210 mg, 5.5 mmol), water (3.0 mL) and tetrahydrofuran (5.0 mL). Then, the resulting compound was treated with methanol solution (5.0 mL) of 7 mmol/L ammonia to obtain Compound 166 (72 mg, 24%).

Workup

  1. customand from the resulting compound, obtained

Sources & evidence

ORD record
ord-4d79083ce4b74639aa020dc6eb3ab821
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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