Ammonia → HCID 23147031, compound

HRID 495286Notes

Reaction equation

HRID 495286 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]([CH3:37])[CH:32]=2)[C:16]=1[CH2:38][CH2:39][O:40][CH3:41])[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]([CH3:37])[CH:32]=2)[C:16]=1[CH2:38][CH2:39][O:40][CH3:41])[CH3:14]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 23147420HCID 23147420, compound

Product 1

HCID 23147031HCID 23147031, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In the same manner as in Example 118, 1-[4,6-bis(methoxycarbonyloxy)-2-(2-methoxyethyl)-3-(3-methylphenyl)phenyl]ethanone was obtained from Compound 122 (320 mg, 1.1 mmol) obtained in Example 122, using methyl chlorocarbonate (0.21 mL, 2.7 mmol), triethylamine (0.37 mL, 2.7 mmol) and tetrahydrofuran (10 mL); and from the resulting compound, obtained was 4-ethyl-1,5-bis(methoxycarbonyloxy)-3-(2-methoxyethyl)-2-(3-methylphenyl)benzene, using sodium borohydride (160 mg, 4.3 mmol), water (5.0 mL) and tetrahydrofuran (10 mL). Then, the resulting compound was treated with methanol solution (10 mL) of 7 mmol/L ammonia to obtain Compound 130 (70 mg, 23%).

Workup

  1. customand from the resulting compound, obtained

Sources & evidence

ORD record
ord-36d3002fe7fd401f9c53ebe0b402b3e2
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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