N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester → N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester

HRID 1592039Notes

Reaction equation

HRID 1592039 reaction equation
[CH2:1]([O:3][C:4](=[O:46])[CH2:5][N:6]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]2[NH:31][C:30](=[O:32])[C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[NH:27][C:26]2=[O:37])=[CH:20][C:19]=1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[S:7]([NH:10]C(OC(C)(C)C)=O)(=[O:9])=[O:8])[CH3:2]>C(Cl)Cl.FC(C(O)=O)(F)F.C([SiH](CC)CC)C>[CH2:1]([O:3][C:4](=[O:46])[CH2:5][N:6]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]2[NH:31][C:30](=[O:32])[C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[NH:27][C:26]2=[O:37])=[CH:20][C:19]=1[O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[S:7]([NH2:10])(=[O:8])=[O:9])[CH3:2]

Participants

3

Reactant 1

HCID 67139078N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester

Product 1

HCID 67138957N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 131726667triethylsilane TFA DCMSolvent

Procedure

The title M compound, N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester (124 mg, 0.19 mmol) is dissolved in CH2Cl2-TFA-triethylsilane (2.5:7:0.5, 1.5 mL) and the solution is stirred at RT for 1 h and evaporated. The residue is dissolved in EtOAc and the solution is washed twice with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and evaporated to give N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester as a foam: [M+1]+=553.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in EtOAc
  3. washthe solution is washed twice with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0226e1e54e924b35a89176880e0c9376
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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