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

HRID 1397538Notes

Reaction equation

HRID 1397538 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 Et2O 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 Et2O

Sources & evidence

ORD record
ord-c18d4ab3f70d4177a07faad6d1e36563
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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