HCID 18391509, compound → trans-4-Carboxy-L-proline

HRID 1586106Notes

Reaction equation

HRID 1586106 reaction equation
C([N:11]1[CH2:18][C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O>CO.[Pd]>[C:19]([C@H:17]1[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1)([OH:21])=[O:20]

Participants

4

Reactant 1

HCID 18391509HCID 18391509, compound

Product 1

HCID 1515192trans-4-Carboxy-L-prolineYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-CBZ-trans-4-carboxy-L-proline (0.458 g, 1.56 mmol) was dissolved in methanol (50 mL) and transferred into a Parr shaker bottle. After adding 10% Pd-C (0.080 g), the mixture was shaken under an atmosphere of hydrogen at 48-50 psi for 0.5 h on the Parr apparatus. The catalyst was removed by filtration through Celite and the filter cake was washed with water. The combined filtrate and washings were concentrated in vacuo to yield a white solid, which was recrystallized from H2O-EtOH-acetone to yield 0.187 g (75%) of 7 as colorless prisms: mp 219°-220° C. (lit. 18 mp 223°-225° C.); [α]25D -54° (c 1.04, H2O) [lit. 18 [α]20D -46.0° (c 1.0, H2O)]; 1H NMR (300 MHz, D2O) δ 4.28 (dd, J=8.6, 7.3 Hz, 1 H, H-2), 3.68-3.57 (m, 2 H, H-5), 3.38-3.29 (m, 1 H, H-4), 2.59 (ddd, J=13.7, 8.6, 6.0 Hz, 1 H, H-3), 2.42 (ddd, J=13.7, 8.1, 7.3 Hz, 1 H, H-3); 13C NMR (75.5 MHz, D2O) δ 178.99, 176.30, 63.67, 50.32, 45.24, 35.18; IR (KBr) 3600-2200 (broad), 1720, 1610, 1515, 1360, 1335, 1285, 1220, 1185 cm -1 ; LRMS (EI, 70 eV) m/e 159 (M+, 19), 114 (100), 87 (53), 68 (92). Anal. Calcd for C6H9NO4 : C, 45.28; H, 5.70; N, 8.80. Found: C, 45.21; H, 5.64; N, 8.68.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter cake was washed with water
  3. concentrationThe combined filtrate and washings were concentrated in vacuo
  4. customto yield a white solid, which
  5. customwas recrystallized from H2O-EtOH-acetone

Sources & evidence

ORD record
ord-12963f56132241408be25f9f707ab7e2
Source dataset
uspto-grants-1999_08
Patent number
US05942537

Reaction notes

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