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

HRID 530695Notes

Reaction equation

HRID 530695 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])[CH2:9][N:8]([C:10](=[O:29])[C@H:11]([NH:21]C(=O)OC(C)(C)C)[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:7]2)[CH2:3][CH2:2]1.[ClH:37]>C(OCC)(=O)C>[ClH:37].[NH2:21][C@H:11]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:10]([N:8]1[CH2:7][C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:9]1)=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86729200tert-butyl [(R)-2-(3-cyclopropylmethoxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate

Product 1

HCID 71152339(R)-2-amino-1-(3-cyclopropylmethoxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.7 g (3.5 mmol) of tert-butyl [(R)-2-(3-cyclopropylmethoxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate are placed in 45 ml of a 3M solution of hydrogen chloride in ethyl acetate and are stirred at room temperature for 3 hours. After evaporation under a stream of nitrogen, the crude product is taken up in a mixture of heptane and ethyl acetate, and then concentrated under vacuum. 1.6 g (100%) of (R)-2-amino-1-(3-cyclopropylmethoxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one hydrochloride are obtained in the form of a beige-coloured solid.

Workup

  1. customAfter evaporation under a stream of nitrogen
  2. additionthe crude product is taken up in a mixture of heptane and ethyl acetate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cce158d99b0847af9881cbb164d67eb0
Source dataset
uspto-grants-2016_05
Patent number
US09353083B2

Reaction notes

Loading…