Triethylamine → 1-Amino-3-benzyloxy-cyclobutanecarboxylic acid ethyl ester

HRID 591085Notes

Reaction equation

HRID 591085 reaction equation
[NH2:1][C:2]1([C:14]([OH:16])=[O:15])[CH2:5][CH:4]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.[CH3:17][CH2:18]N(CC)CC.O=S(Cl)Cl>C(O)C>[CH2:17]([O:15][C:14]([C:2]1([NH2:1])[CH2:5][CH:4]([O:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:3]1)=[O:16])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 106089941-Amino-3-(benzyloxy)cyclobutanecarboxylic acid

Product 1

HCID 666464711-Amino-3-benzyloxy-cyclobutanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a reactor charged with 1-amino-3-benzyloxy-cyclobutanecarboxylic acid (202.7 g, 0.94 mol) was added ethanol (7.0 l); the mixture was stirred at ambient temperature with mechanical stirring under an N2-atmosphere for 18 minutes. To the reaction mixture was added Et3N (350 ml, 2.51 mol), cooled to −1.8° C. and SOCl2 (170 ml, 2.4 mol) was added carefully keeping the reaction temperature <10° C. The reaction mixture was refluxed for 20 hours 10 minutes (reaction progress followed by TLC monitoring). Upon complete reaction the reaction mixture was cooled to 20° C. and evaporated in vacuo at 35° C. The weight of crude product including salts was 631.2 g.

Workup

  1. stirringwith mechanical stirring under an N2-atmosphere for 18 minutes
  2. temperaturecooled to −1.8° C.
  3. customthe reaction temperature <10° C
  4. temperatureThe reaction mixture was refluxed for 20 hours 10 minutes
  5. custom(reaction progress followed by TLC monitoring)
  6. customUpon complete reaction the reaction mixture
  7. temperaturewas cooled to 20° C.
  8. customevaporated in vacuo at 35° C

Sources & evidence

ORD record
ord-b868918f277e43c0ab6960148446d511
Source dataset
uspto-grants-2016_01
Patent number
US09238596B2

Reaction notes

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