Ammonia → HCID 23147011, compound

HRID 495293Notes

Reaction equation

HRID 495293 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][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]([CH3:37])[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 23147585HCID 23147585, compound

Product 1

HCID 23147011HCID 23147011, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In the same manner as in Example 118, 1-{4,6-bis(methoxycarbonyloxy)-2-[2-(2-methoxyethoxy)ethyl]-3-(3-methylphenyl)phenyl}ethanone was obtained from Compound 139 (410 mg, 1.2 mmol) obtained in Example 139, using methyl chlorocarbonate (0.2 mL, 2.6 mmol), triethylamine (0.4 mL, 2.9 mmol) and tetrahydrofuran (5.0 mL); and from the resulting compound, obtained was 4-ethyl-1,5-bis(methoxycarbonyloxy)-3-[2-(2-methoxyethoxy)ethyl]-2-(3-methylphenyl)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 149 (180 mg, 45%).

Workup

  1. customand from the resulting compound, obtained

Sources & evidence

ORD record
ord-cfb7a3c1cac349ba810a364b600b0c29
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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