1-Hydroxybenzotriazole → N-(benzyl-sulfonyl)-D-tryptophyl-N1-(4-aminobenzyl)-L-methioninamide

HRID 890928Notes

Reaction equation

HRID 890928 reaction equation
[CH2:1]([S:8]([NH:11][C@@H:12]([C:17]([NH:19][C@H:20]([C:25](O)=[O:26])[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[C@@H:13]([CH2:15][CH3:16])C)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1.[CH:37]1[CH:38]=[CH:39][C:40]2N(O)N=[N:43][C:41]=2[CH:42]=1.CCN=C=NCCCN(C)C.Cl>ClCCl>[CH2:1]([S:8]([NH:11][C@@H:12]([C:17]([NH:19][C@H:20]([C:25]([NH:34][CH2:33][C:32]1[CH:35]=[CH:36][C:29]([NH2:28])=[CH:30][CH:31]=1)=[O:26])[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[CH2:13][C:15]1[C:40]2[C:41](=[CH:42][CH:37]=[CH:38][CH:39]=2)[NH:43][CH:16]=1)(=[O:10])=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 4278144-AminobenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69623728N-(benzylsulfonyl)-D-isoleucyl-L-methionine

Product 1

HCID 69623691N-(benzyl-sulfonyl)-D-tryptophyl-N1-(4-aminobenzyl)-L-methioninamideYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(benzylsulfonyl)-D-isoleucyl-L-methionine (100 mg, 0.24 mmol) and 4-aminobenzylamine (59 mg, 0.48 mmol) in dichloromethane (5 ml), HOBt (44 mg, 0.29 mmol) and EDC HCl (56 mg, 0.29 mmol) were added and stirred at room temperature under a nitrogen stream. After 12 hours, the reaction mixture was concentrated under reduced pressure and water was added to the residue. The precipitated product was collected by filtration, washed with water and then dried. The resulting crude product was applied to column chromatography (Fuji Silysia NH-DM-1020; mobile phase: dichloromethane:methanol=10:1) to give N-(benzyl-sulfonyl)-D-tryptophyl-N1-(4-aminobenzyl)-L-methioninamide (108 mg, 0.21 mmol; yield 86%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5505bc46cc294ad5abaec213cf2c38b7
Source dataset
uspto-grants-2006_02
Patent number
US07001887B2

Reaction notes

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