Diisopropylethylamine → (2R,4R)-5-(4-Bromophenyl)-2-hydroxy-4-[(3-hydroxy-3H-benzotriazole-5-carbonyl)-amino]-pentanoic Acid Ethyl Ester

HRID 2273485Notes

Reaction equation

HRID 2273485 reaction equation
CN(C(ON1N=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:26][N:27]1[C:31]2[CH:32]=[C:33]([C:36]([OH:38])=O)[CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1.CCN(C(C)C)C(C)C.[CH2:48]([O:50][C:51](=[O:65])[C@H:52]([OH:64])[CH2:53][C@H:54]([NH2:63])[CH2:55][C:56]1[CH:61]=[CH:60][C:59]([Br:62])=[CH:58][CH:57]=1)[CH3:49]>>[CH2:48]([O:50][C:51](=[O:65])[C@H:52]([OH:64])[CH2:53][C@H:54]([NH:63][C:36]([C:33]1[CH:34]=[CH:35][C:30]2[N:29]=[N:28][N:27]([OH:26])[C:31]=2[CH:32]=1)=[O:38])[CH2:55][C:56]1[CH:57]=[CH:58][C:59]([Br:62])=[CH:60][CH:61]=1)[CH3:49]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 24237871-hydroxy-1H-1,2,3-benzotriazole-6-carboxylic acidHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 67969401(2R,4R)-4-amino-5-(4-bromophenyl)-2-hydroxypentanoic acid ethyl ester

Product 1

HCID 67969686(2R,4R)-5-(4-Bromophenyl)-2-hydroxy-4-[(3-hydroxy-3H-benzotriazole-5-carbonyl)-amino]-pentanoic Acid Ethyl EsterYield 76.5%

Procedure

HCTU (837 mg, 2.0 mmol) was added to a solution of 1-hydroxy-1H-1,2,3-benzotriazole-6-carboxylic acid (362 mg, 2.0 mmol) and the mixture was stirred at room temperature for 10 minutes. DIPEA (529 μL, 3.0 mmol) and (2R,4R)-4-amino-5-(4-bromophenyl)-2-hydroxy-pentanoic acid ethyl ester (320 mg, 1.0 mmol) were then added and the resulting mixture was stirred at room temperature for 15 minutes. The mixture was concentrated in vacuo and the resulting residue was purified (C18 column, 55 g, 20-70% MeCN in water with 5% TFA) to yield the title compound as a white solid 365 mg).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 15 minutes
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe resulting residue was purified (C18 column, 55 g, 20-70% MeCN in water with 5% TFA)

Sources & evidence

ORD record
ord-d45f18bb1d724e53aa2800dd4caa1f51
Source dataset
uspto-grants-2015_09
Patent number
US09120747B2

Reaction notes

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