Methyl iodide → HCID 131720707, compound

HRID 963852Notes

Reaction equation

HRID 963852 reaction equation
C1([N:4](CCCO)[C:5]([CH2:7][C@H:8]([NH:26][S:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)(=[O:29])=[O:28])[C:9]([NH:11]C[C@@H]2CCCN(N(C=N)C(=O)OC)C2)=[O:10])=[O:6])CC1.CI.C(Cl)Cl>C1COCC1.C1CCN2C(=NCCC2)CC1>[CH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:38]=[CH:39][C:30]=1[S:27]([NH:26][CH:8]([CH2:7][C:5]([NH2:4])=[O:6])[C:9]([NH2:11])=[O:10])(=[O:29])=[O:28]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 131720708HCID 131720708, compound

Product 1

HCID 131720707HCID 131720707, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Procedure

274 mg of methyl [(S)-3-[(S)-3-[cyclopropyl-(3-hydroxypropyl)-carbamoyl]-2-(naphthalen-2-ylsulfonylamino)-propionylaminomethyl]-piperidin-1-yl]-imino-methylcarbamate (Example 63), 1 ml of 1N methyl iodide in THF, 2 ml of 1 molar DBU solution in THF and 2 ml of methylene chloride are stirred together at room temperature. The mixture is concentrated and the residue is chromatographed over silica gel with ethyl acetate-methanol 9:1. There are obtained 120 mg of (S)-N1-cyclopropyl-N4-[(S)-1-(iminomethoxycarbonylamino-methyl)-piperidin-3-ylmethyl]-N1-(3-methoxy-propyl)-2-(naphthalen-2-ylsulfonylamino-succinamide, MS (ISO): 631.6 (M+H).

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is chromatographed over silica gel with ethyl acetate-methanol 9:1

Sources & evidence

ORD record
ord-835d62137ab141a2a2908702860d134d
Source dataset
uspto-grants-1998_06
Patent number
US05763604

Reaction notes

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