Triethylamine → HCID 18390924, compound

HRID 1584410Notes

Reaction equation

HRID 1584410 reaction equation
[NH2:1][C@@H:2]([CH2:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:3]([NH:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:4].[C:28]([NH:38][C@H:39]([C:43](O)=[O:44])[CH:40]([CH3:42])[CH3:41])([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[C:7]([O:6][NH:5][C:3](=[O:4])[C@@H:2]([NH:1][C:43](=[O:44])[C@H:39]([CH:40]([CH3:41])[CH3:42])[NH:38][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][CH:20]=1)(=[O:13])=[O:14])([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 54213503HCID 54213503, compound

Product 1

HCID 18390924HCID 18390924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-amino-N-tert-butoxy-3-(4-phenoxyphenylsulfonyl)-propionamide (1.9 g) in methylene chloride (30 ml) was added CBZ-(S)-valine (1.6 g), 1-hydroxybenzotriazole (0.9 g), triethylamine (1 ml), and N'-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide (1.3 g). After stirring overnight at room temperature, the solution was partitioned between methylene chloride and water, and after the organic layer was dried over magnesium sulfate, solvent was removed under reduced pressure to give (R)-N-tert-butoxy-2-(CBZ-valinamido)-3-(4-phenoxyphenylsulfonyl)-propionamide, which was used without further purification.

Workup

  1. customthe solution was partitioned between methylene chloride and water
  2. dry with materialafter the organic layer was dried over magnesium sulfate, solvent
  3. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-fa2523a040584d67badf2212eb63b821
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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