Hydrochloric Acid → (1R,2S,3R,5R)-3-Amino-5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate hydrochloride

HRID 1677936Notes

Reaction equation

HRID 1677936 reaction equation
[C:1]([O:9][C@@H:10]1[C@@H:14]([CH2:15][OH:16])[CH2:13][C@@H:12]([NH:17]C(OC(C)(C)C)=O)[C@@H:11]1[O:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:34].O1CCOCC1>>[ClH:34].[C:1]([O:9][C@@H:10]1[C@@H:14]([CH2:15][OH:16])[CH2:13][C@@H:12]([NH2:17])[C@@H:11]1[O:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59671317(1R,2S,3R,5R)-3-[(tert-Butoxycarbonyl)amino]5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate

Product 1

HCID 66797769(1R,2S,3R,5R)-3-Amino-5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate hydrochlorideYield 90%

Procedure

(1R,2S,3R,5R)-3-[(tert-Butoxycarbonyl)amino]-5-(hydroxymethyl)-cyclopentane-1,2-diyl dibenzoate (1.42 g, 3.11 mmol) was treated with a 4.00 M solution of HCl in 1,4-dioxane (17.0 mL, 69.3 mmol) and the reaction was stirred for 35 min. The reaction mixture was concentrated in vacuo and Et2O was added to precipitate the product, which was washed with Et3O to afford the title compound as a white solid (1.05 g, 90%). LC/MS: Rt=1.06 min, ES− 356 (FA standard).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and Et2O
  2. additionwas added
  3. customto precipitate the product, which
  4. washwas washed with Et3O

Sources & evidence

ORD record
ord-240b2c0e843642bba65e9d746dcbade3
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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