Ethyl formate → HCID 73977853, compound

HRID 595142Notes

Reaction equation

HRID 595142 reaction equation
[NH2:1][C:2]1[C:17]([C:18](=[O:20])[CH3:19])=[CH:16][C:5]2[O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][C:4]=2[CH:3]=1.C[O-].[Na+].[CH:24](OCC)=O>COCCOC.O>[NH:1]1[C:2]2[CH:3]=[C:4]3[O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][C:5]3=[CH:16][C:17]=2[C:18](=[O:20])[CH:19]=[CH:24]1

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 10942334Sodium Methoxide2×HCID 86684832HCID 86684832, compound

Product 1

HCID 73977853HCID 73977853, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-(3-Amino-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone (108 mmol, 29.3 g) in DME (700 ml) was added sodium methoxide (432 mmol, 23.35 g). The mixture was stirred for 30 minutes. Ethyl formate (540 mmol, 44 ml) was added and the mixture was stirred overnight. (Additional sodium methoxide may be needed if reaction is not complete as monitored by LC/MS.) After the reaction was completion, the mixture was diluted with water (40 ml) and acidified to neutral with 1M HC 1. The precipitate was filtered and washed with water, dried in vacuo to afford 22 g (72%) of 7,8,10,11,13,14-Hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalen-4-one. 1HNMR (400 MHz, DMSO) δ 8.58 (s, 1H), 7.52 (s, 1H), 7.22 (s, 1H), 7.12 (m, 1H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H). LC/MS Calcd for (M+H)+292.3. found 292.5.

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ccba7d066a134d0284ca10538eb1afe1
Source dataset
uspto-grants-2016_01
Patent number
US09242991B2

Reaction notes

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