1,2-Dichloroethane → HCID 59714664, compound

HRID 2223155Notes

Reaction equation

HRID 2223155 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[NH2:19])=[O:12])=[CH:6][CH:5]=1)[CH3:2].[C:20]([NH:27][C@@H:28]([C:30](O)=[O:31])[CH3:29])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[C:23]([O:22][C:20](=[O:21])[NH:27][C@@H:28]([C:30](=[O:31])[NH:19][C:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C:13]=1[C:11](=[O:12])[NH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=1)[CH3:29])([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 637606BOC-D-alanineHCID 58617375HCID 58617375, compound

Product 1

HCID 59714664HCID 59714664, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-amino-cyclohex-1-enecarboxylic acid (4-ethoxy-phenyl)-amide (1.46 g, 5.60 mmol), N-Boc-D-alanine (1.06 g, 5.60 mmol), EDC (1.60 g, 8.4 mmol), HOBT (151 mg, 1.12 mmol) and 1.0 mL of N-methylmorpholine in 30 mL of methylene chloride was allowed to stir at room temperature for 28 h. Upon completion, the mixture was concentrated and 30 mL of saturated aqueous sodium bicarbonate was added. The resulting mixture was extracted with ethyl acetate (30 mL×3). The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The material was purified by chromatography on a silica gel column using 30% ethyl acetate/hexane successively as the eluents to give 1.53 g of product H4. 1H NMR (400 MHz, CDCl3) δ: 12.95 (s, 1H), 7.36 (d, J=8.86 Hz, 2H), 7.25 (br s, 1H), 8.87 (d, J=8.95 Hz, 2H), 5.23 (br s, 1H), 4.13 (br s, 1H), 4.02 (q, J=7.0 Hz, 2H), 3.01 (br s, 2H), 2.37 (br s, 2H), 1.70 (m, 4H), 1.43 (s, 9H), 1.41 (dd, J=7.0, 7.0 Hz, 3H), 1.40 (obscured d, J=7.07 Hz, 3H). MS (ESI+) 432 [M+H]+.

Workup

  1. concentrationUpon completion, the mixture was concentrated
  2. addition30 mL of saturated aqueous sodium bicarbonate was added
  3. extractionThe resulting mixture was extracted with ethyl acetate (30 mL×3)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe material was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-e9955bb41e4742d680cd01b2d2a58c87
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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