Hydrochloric Acid → (R)-2-amino-1-(3-but-2-ynyloxy-3-o-tolyl-azetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one

HRID 540433Notes

Reaction equation

HRID 540433 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:14][C:13]([O:22][CH2:23][C:24]#[C:25][CH3:26])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:12]1)=[O:10])(C)(C)C.Cl>C(OCC)(=O)C>[NH2:7][C@H:8]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)[C:9]([N:11]1[CH2:12][C:13]([O:22][CH2:23][C:24]#[C:25][CH3:26])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:14]1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67295764tert-butyl[(R)-2-(3-but-2-ynyloxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxo-ethyl]carbamate

Product 1

HCID 66988366(R)-2-amino-1-(3-but-2-ynyloxy-3-o-tolyl-azetidin-1-yl)-3-(4-methoxyphenyl)propan-1-oneYield 116.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.7 g (3.5 mmol) of tert-butyl[(R)-2-(3-but-2-ynyloxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxo-ethyl]carbamate are solubilised in 45 ml (135 mmol) of a 3M solution of hydrochloric acid in ethyl acetate. After stirring for 3 h at ambient temperature, the mixture is concentrated. 1.6 g of (R)-2-amino-1-(3-but-2-ynyloxy-3-o-tolylazetidin-1-yl)-3-(4-methoxyphenyl)-propan-1-one are obtained in the form of a beige solid with a quantitative yield.

Workup

  1. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-8c6b4f87d9334b44a5f9a0cdf70a3259
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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