1,2-Dichloroethane → [5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-thioacetic acid S-benzyl ester

HRID 270535Notes

Reaction equation

HRID 270535 reaction equation
O[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:31]([S:38][C:39](=[O:42])[CH2:40][NH2:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.CN(C=O)C>[CH2:31]([S:38][C:39](=[O:42])[CH2:40][NH:41][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:16]2[NH:15][C:13](=[O:14])[NH:12][CH:11]2[CH2:10][S:9]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 171548BiotinHCID 86206484S-benzyl 2-aminoethanethioate

Product 1

HCID 11524320[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-thioacetic acid S-benzyl esterYield 42.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Biotin 19 (0.156 g, 0.64 mmol) was dissolved in 40 mL of dry THF. To this solution was added EDC (0.123 g, 0.64 mmol) and HOBt (0.098 g, 0.64 mmol) under ice-cold conditions. The reaction was allowed to stir for 30 minutes, followed by addition of 8 (0.139 g, 0.64 mmol) dissolved in minimal amount of DMF. The resulting solution was allowed to stir overnight at RT. Upon removal of the solvent in vacuo, the residue was taken into ethyl acetate and washed with 1 N HCl (2×30 ml), water (2×30 ml) and brine (2×30 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 5 (0.110 g, 42%). 1H-NMR (300 MHz, DMSO) δ 7.31-7.28 (m, 5H), 6.40-6.35 (broad, 2H), 4.37-4.32 (m, 2H), 4.22 (d, J=5.61 Hz, 2H), 4.09 (s, 2H), 3.1-3.0 (m, 1H), 2.88-2.78 (m, 2H), 2.19-2.14 (m, 2H), 1.60-1.48 (m, 6H). MS (ESI): m/z 408.0 [(M+1)]+.

Workup

  1. stirringto stir overnight at RT
  2. customUpon removal of the solvent in vacuo
  3. washwashed with 1 N HCl (2×30 ml), water (2×30 ml) and brine (2×30 ml)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87f2a8d71fe64fe6bf1dafe8af1bd555
Source dataset
uspto-grants-2008_11
Patent number
US07449558B2

Reaction notes

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