HCID 178462112, compound → HCID 178462113, compound

HRID 862228Notes

Reaction equation

HRID 862228 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[N:11]=[C:12]([C:15]([NH:17][C@@H:18]([C:20]([NH:22][C@H:23]3[CH2:27][C:26](=[O:28])[O:25][C@@H:24]3[O:29]CC3C=CC=CC=3)=[O:21])[CH3:19])=[O:16])[NH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CO>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[N:11]=[C:12]([C:15]([NH:17][C@H:18]([C:20]([NH:22][C@H:23]([CH:24]=[O:29])[CH2:27][C:26]([OH:28])=[O:25])=[O:21])[CH3:19])=[O:16])[NH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 178462112HCID 178462112, compound

Product 1

HCID 178462113HCID 178462113, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2R,S,3S)N2 -[4-(3-Phenylpropyl)imidazole-2-carbonyl]-N-(tetrahydro-2-benzyloxy-5-oxo-3-furanyl)-L-alaninamide (0.93 g, 1.90 mmol) and 10% palladium on activated carbon (0.93 g) in methanol (100 ml) was stirred under a hydrogen atmosphere for 5 h. The resulting mixture was filtered and concentrated to yield a colorless glass. Recrystallization from methanol-diethyl ether afforded 401 mg (53%) of 20d as a colorless solid: mp. 94°-96° C.; [α]D27 +16.4° (c 0.5, MeOH); IR (KBr) 3300, 3287, 1786, 1732, 1659, 1651, 1532, 1451; 1H NMR(CD3OD) δ 7.19 (5H, m), 6.91 (1H, s), 4.60-4.46 (2H, m), 4.27 (1H, m), 2.63 (4H, m), 2.75-2.40 (2H, m), 1.96 (2H, m), 1.44 (3H, d, J=7.0).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated
  3. customto yield a colorless glass
  4. customRecrystallization from methanol-diethyl ether

Sources & evidence

ORD record
ord-df6a5cb27760434aa29b2544dc4f4bf8
Source dataset
uspto-grants-1998_02
Patent number
US05716929

Reaction notes

Loading…