1,2-Dichloroethane → (S)-methyl 3-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamoyl)benzoate

HRID 2355502Notes

Reaction equation

HRID 2355502 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=O)[CH:3]=1.[NH2:14][C@@H:15]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:16][N:17]([CH3:27])[C:18](=[O:26])[O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:29]1([CH2:28][C@H:15]([NH:14][C:5]([C:4]2[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=2)[C:1]([O:12][CH3:13])=[O:11])=[O:7])[CH2:16][N:17]([CH3:27])[C:18]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:26])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69512791,3-Benzenedicarboxylic acid, monomethyl esterHCID 593829982-(trimethylsilyl)ethyl (S)-2-amino-3-cyclohexylpropylmethylcarbamate

Product 1

HCID 67192450(S)-methyl 3-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of mono-methyl isophthalate (0.3230 g, 1.79 mmol, 1.0 equiv), 2-(trimethylsilyl)ethyl (S)-2-amino-3-cyclohexylpropylmethylcarbamate (0.5573 g, 1.77 mmol, 0.99 equiv), EDC (0.6200 g, 1.8 equiv), HOBT (0.4035 g, 1.66 equiv), and DIEA (3.6 mL, 11 equiv) in CH2Cl2 (20 mL) was stirred at rt for 18 h. The reaction mixture was quenched with 10% aq Na2CO3, extracted with CH2Cl2 and dried over Na2SO4. After the solvent was removed, the crude (S)-methyl 3-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamoyl)benzoate (1.397 g) was used in the next step without further purification. LC-MS (3 min) tR=2.29 min, m/z 499 (M+Na+), 449, 359.

Workup

  1. customThe reaction mixture was quenched with 10% aq Na2CO3
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed
  5. customthe crude (S)-methyl 3-(1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamoyl)benzoate (1.397 g) was used in the next step without further purification
  6. customLC-MS (3 min) tR=2.29 min, m/z 499 (M+Na+), 449, 359

Sources & evidence

ORD record
ord-b71ee0edae604052b36657334df4af0d
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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