(4R)-1-(tert-Butoxycarbonyl)-4-cyano-D-proline → HCID 14842647, compound

HRID 893057Notes

Reaction equation

HRID 893057 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([C:16]#[N:17])[CH2:13][C@@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1C[C@H](CN)C[C@H]1C(O)=O)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@@H:14]([CH2:16][NH2:17])[CH2:13][C@@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 14842643(4R)-1-(tert-Butoxycarbonyl)-4-cyano-D-prolineHCID 14842646(4S)-4-(Aminomethyl)-1-(tert-butoxycarbonyl)-L-proline

Product 1

HCID 14842647HCID 14842647, compoundYield 95%

Procedure

Cyano acid 28 (650 mg, 2.7 mmol) was hydrogenated as for the synthesis of 12, and the produce was crystallized from water/ethanol/ether to give 630 mg (95% yield), m.p.=187°-189° C. (decomposition). 1H NMR (D2O) δ 1.40/1.44 (2s, 9H), 1.62 (m, 1H). 2.55 (m, 2H), 3.13 (m, 2H), 3.75 (m, 2H), 4.10 (m, 1H). Anal. (C11H20N2O4).

Workup

  1. customthe produce was crystallized from water/ethanol/ether
  2. customto give 630 mg (95% yield), m.p.=187°-189° C. (decomposition)

Sources & evidence

ORD record
ord-c8e4ff29e4684e9db5bd0d1d50531529
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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