HCID 58864226, compound → HCID 58864364, compound

HRID 1353539Notes

Reaction equation

HRID 1353539 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@H:4]([NH:25]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]1[CH:24]=[CH:23][C:9]2[N:10]=[C:11]([CH3:22])[N:12]([S:13]([CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])(=[O:15])=[O:14])[C:8]=2[CH:7]=1.COC(=O)[C@H](NC(OCC1C=CC=CC=1)=O)CC1C=CC2N(S(CC[Si](C)(C)C)(=O)=O)C(C)=NC=2C=1.[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:36])[C@H:4]([NH2:25])[CH2:5][C:6]1[CH:24]=[CH:23][C:9]2[N:10]=[C:11]([CH3:22])[N:12]([S:13]([CH2:16][CH2:17][Si:18]([CH3:19])([CH3:21])[CH3:20])(=[O:14])=[O:15])[C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 58864226HCID 58864226, compoundHCID 58864410HCID 58864410, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58864364HCID 58864364, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A methanol (50 mL) suspension of (R)-2-benzyloxycarbonylamino-3-[2-methyl-3-(2-trimethylsilanyl-ethanesulfonyl)-3H-benzoimidazol-5-yl]-propionic acid methyl ester and (R)-2-Benzyloxycarbonylamino-3-[2-methyl-1-(2-trimethylsilanyl-ethanesulfonyl)-1H-benzoimidazol-5-yl]-propionic acid methyl ester (1:1 mixture, 600 mg), and 10% palladium on charcoal (180 mg) was agitated on a Parr apparatus overnight under 40 psi of hydrogen at room temperature. After replacing the hydrogen atmosphere with nitrogen, the mixture was filtered through a pad of celite. Solvents were removed in vacuo to afford the title compound as a tan solid (80%). 1H-NMR (CD3OD, 500 MHz) δ 7.81 (d, J=8.5, 0.5 Hz, 0.5H), 7.70 (s, 0.5H), 7.58 (d, J=8.5 Hz, 0.5H), 7.49 (s, 0.5H), 7.25 (d, J=9.0 Hz, 1H), 3.89 (dd, J=14.0, 6.5 Hz, 1H), 3.75 (s, 1.5H), 3.72 (s, 1.5H), 3.55–3.51 (m, 2H), 3.18 (d, J=6.0 Hz, 1H), 3.22–3.18 (m, 0.5H), 3.14–3.09 (m, 0.5H), 2.81 (s, 1.5H), 2.80 (s, 1.5H), 0.92–0.88 (m, 2H), 0.02 (s, 4.5H), 0.01 (s, 4.5H); 13CNMR (CD3OD, 125 MHz) δ 174.3, 174.1, 153.5, 153.3, 141.7, 140.6, 133.9, 133.82, 133.78, 132.7, 126.5, 126.3, 119.7, 119.0, 114.1, 113.4, 55.6, 51.8, 51.7, 51.6, 40.2, 39.8, 15.83, 15.77, 9.9, −3.07, −3.11. Mass spec.: 398.20 (MH)+.

Workup

  1. filtrationthe mixture was filtered through a pad of celite
  2. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-afad6c04345c4a15a9b53613069c19b6
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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