1-Hydroxybenzotriazole → [(2R,3S)-2-Hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl ester

HRID 852574Notes

Reaction equation

HRID 852574 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:15]=1)[C:10]([OH:12])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:45]([O:52][C:53](=[O:67])[NH:54][CH2:55][C@@H:56]([OH:66])[C@@H:57]([NH2:65])[CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(Cl)Cl>[CH2:45]([O:52][C:53](=[O:67])[NH:54][CH2:55][C@@H:56]([OH:66])[C@@H:57]([NH:65][C:10]([C:9]1[CH:13]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:15]=[C:7]([N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[CH:8]=1)=[O:12])[CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 693571053-(2-Oxo-pyrrolidin-1-yl)-5-pentyloxy-benzoic acidHCID 69358558phenylmethyl [(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]carbamate hydrochloride

Product 1

HCID 69359603[(2R,3S)-2-Hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzoic acid (A13) (530 mg, 1.82 mmol, 1 equiv) in CH2Cl2 (20 ml) were added HOBT (300 mg, 2.2 mmol, 1.2 equiv) and EDAC.HCl (420 mg, 2.2 mmol, 1.2 equiv). After stirring for 5 min, 3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzoic acid hydrochloride (D104) (570 mg, 1.82 mmol, 1 equiv) was added and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with CH2Cl2 (20 ml) washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give [(2R,3S)-2-hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl ester (D105) (510 mg, 48%) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 h
  2. washwashed with saturated aqueous NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d2d8f6aacb7402e83b76fcba3c7e590
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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