1,2-Dichloroethane → HCID 59382925, compound

HRID 451783Notes

Reaction equation

HRID 451783 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:31][C:29]=2C=1.CCN(C(C)C)C(C)C.CN.CCO>C(Cl)Cl>[CH3:29][NH:31][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH:14]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 702EthanolHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57544653HCID 57544653, compound

Product 1

HCID 59382925HCID 59382925, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-(4-methylcyclohexyl)propanoic acid (2.080 g, 7.29 mmol, 1.0 equiv), EDC (3.308 g, 2.37 equiv), HOBT (1.752 g, 1.78 equiv), DIEA (7.6 mL, 6 equiv) and 33% wt. methylamine in EtOH (2.771 g, 4 equiv) in CH2Cl2 (80 mL) was stirred at rt for 21 h. The solvents were removed in vacuo and 200 mL of 1 N HCl was added. The mixture was extracted three times with EtOAc, washed with brine, and dried over Na2SO4. After the solvents were removed in vacuo, the residue was purified by reversed-phase HPLC to give 1.0167 g (47%) of (S)-tert-butyl 1-(methylamino)-3-(4-methylcyclohexyl)-1-oxopropan-2-ylcarbamate. MS ESI +ve m/z 321 (M+Na). 1H NMR (CDCl3, 400 MHz) δ 6.27 (br s, 1H), 4.91 (br s, 1H), 4.11-4.07 (m, 1H), 2.80, 2.79 (d, J=4.8 Hz, 3H), 1.85-1.20 (m, 21H), 0.88, 0.85 (d, J=6.4 Hz, 3H).

Workup

  1. customThe solvents were removed in vacuo and 200 mL of 1 N HCl
  2. additionwas added
  3. extractionThe mixture was extracted three times with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter the solvents were removed in vacuo
  7. customthe residue was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-0091a54b94ec4c68be489a659684a3a4
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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