HCID 131727245, compound → HCID 85850727, compound

HRID 1454339Notes

Reaction equation

HRID 1454339 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])([OH:13])[CH2:9]1)=O)(C)(C)C>Cl.CCO>[OH:13][C:10]1([P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 131727245HCID 131727245, compound

Product 1

HCID 85850727HCID 85850727, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 1.78 g (5.5 mmol) of (R/S)-1-tert-butoxycarbonyl-3-hydroxy-pyrrolidin-3-yl phosphonic acid, diethyl ester (from Step C) in 2N HCl in EtOH was stirred at rt for 5.5 h. The reaction was concentrated from CH2Cl2 several times. The crude product was partitioned between aqueous NH4OH and CHCl3/isopropanol (3:1 v/v). After separating phases, the aqueous layer was extracted with 3× CHCl3/isopropanol (3:1 v/v). The combined organics were dried over Na2SO4 and concentrated. The residue was purified on a 40S Biotage column using 90:10:1 v/v/v CH2Cl2/MeOH/NH4OH as the eluant to afford the title compound as a light brown oil: 1H-NMR (500 MHz) δ 1.35 (t, J=7.0, 6H), 1.92 (m, 1H), 2.20 (m, 1H), 2.78-2.99 (m, 3H), 3.06 (dd, J=12.7, 3.7, 1H), 3.13 (dd, J=12.7, 6.2, 1H), 3.20 (m, 1H), 4.16-4.23 (m, 4H).

Workup

  1. concentrationThe reaction was concentrated from CH2Cl2 several times
  2. customThe crude product was partitioned between aqueous NH4OH and CHCl3/isopropanol (3:1 v/v)
  3. customAfter separating phases
  4. extractionthe aqueous layer was extracted with 3× CHCl3/isopropanol (3:1 v/v)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified on a 40S Biotage column

Sources & evidence

ORD record
ord-d001842697934d619ddd3364e27c8ed2
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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