Hydrochloric Acid → (R)-2-amino-1-(3-butoxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydrochloride

HRID 540385Notes

Reaction equation

HRID 540385 reaction equation
[ClH:1].[CH2:2]([O:6][C:7]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])[CH2:10][N:9]([C:11](=[O:30])[C@H:12]([NH:22]C(=O)OC(C)(C)C)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:8]1)[CH2:3][CH2:4][CH3:5]>C(OCC)(=O)C>[ClH:1].[NH2:22][C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:11]([N:9]1[CH2:8][C:7]([O:6][CH2:2][CH2:3][CH2:4][CH3:5])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])[CH2:10]1)=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86659074tert-butyl [(R)-2-(3-butoxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate

Product 1

HCID 66988286(R)-2-amino-1-(3-butoxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6 ml of a 4N solution of hydrochloric acid in ethyl acetate are added to 615 mg (1.24 mmol) of tert-butyl [(R)-2-(3-butoxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate (procedure identical to 4-3). The reaction mixture is stirred at ambient temperature for 2 hours. The precipitate obtained is filtered off, washed with diethyl ether and then dissolved in methanol, followed by evaporation of the solvents. 441 mg of (R)-2-amino-1-(3-butoxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydrochloride are obtained in the form of a white powder with a yield of 82%.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with diethyl ether
  4. dissolutiondissolved in methanol
  5. customfollowed by evaporation of the solvents

Sources & evidence

ORD record
ord-ac09a51ef7f441638b75fac62d9fc8ce
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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