Triethylamine → 2-[4-(4-Pentanoylamino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737160Notes

Reaction equation

HRID 737160 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:43])[CH2:39][CH2:40][CH2:41][CH3:42]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:38](=[O:43])[CH2:39][CH2:40][CH2:41][CH3:42])=[CH:27][CH:28]=2)[N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 86616427(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 765827752-[4-(4-Pentanoylamino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

80 mg (0.19 mmol)) of Compound 5050 was dissolved in 5 mL of dry methylene chloride. To this solution at 0° C. was added triethylamine (0.19 mmol, 25 μL) followed by pentanoyl chloride (0.19 mmol, 22 μL). Reaction mixture was stirred at 0° C. for 15 minutes. Reaction mixture was quenched using water and evaporated. It was redissolved in 5 mL of DMF and purified using reverse phase HPLC. MS: 507.2 (M+H+).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. customwas quenched
  4. customevaporated
  5. dissolutionIt was redissolved in 5 mL of DMF
  6. custompurified

Sources & evidence

ORD record
ord-49cc3d4e8b9944f197ff9ac3ed3e9618
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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