Triethylamine → HCID 69214775, compound

HRID 2182597Notes

Reaction equation

HRID 2182597 reaction equation
CCN(CC)CC.Cl.[CH3:9][O:10][C:11](=[O:17])[C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[Cl:18][C:19]1[CH:20]=[C:21]([N:26]=[C:27]=[O:28])[CH:22]=[C:23]([Cl:25])[CH:24]=1>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:17])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:27](=[O:28])[NH:26][C:21]1[CH:22]=[C:23]([Cl:25])[CH:24]=[C:19]([Cl:18])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 944603,5-Dichlorophenyl isocyanateHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 69214775HCID 69214775, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (1.7 mL) was added to an ice-cold solution of (S)proline methyl ester hydrochloride (1.31 g) and 3,5-dichlorophenylisocyanate (1,97 g) in CH2Cl2 (40 mL). The mixture was stirred for 3 hours. It was washed with water, brine, dried (MgSO4), filtered, and concentrated. Purification by chromatography (Silica gel: EtOAc/hexane: 1/3) afforded (S)-N-[N-(3,5-dichlorophenyl)carbamoyl]proline methyl ester (2.27 g). mp. 110-112° C.; MS (m/z) 339 (M++Na).

Workup

  1. washIt was washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by chromatography (Silica gel: EtOAc/hexane: 1/3)

Sources & evidence

ORD record
ord-799e208faf094ee6a0add9598437ecc0
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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