Ammonia → HCID 23147219, compound

HRID 495291Notes

Reaction equation

HRID 495291 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]([O:37][CH3:38])[CH:32]=2)[C:16]=1[CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH3:45])[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]([O:37][CH3:38])[CH:32]=2)[C:16]=1[CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH3:45])[CH3:14]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 23147304HCID 23147304, compound

Product 1

HCID 23147219HCID 23147219, compoundYield 46%

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-methoxyphenyl)phenyl}ethanone was obtained from Compound 137 (250 mg, 0.69 mmol) obtained in Example 137, using methyl chlorocarbonate (0.15 mL, 1.9 mmol), triethylamine (0.26 mL, 1.9 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-methoxyphenyl)benzene, using sodium borohydride (120 mg, 3.2 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 138 (110 mg, 46%).

Workup

  1. customand from the resulting compound, obtained

Sources & evidence

ORD record
ord-8feaeb6f82064291890a86b679fa9bd9
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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