1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic Acid 4-nitrooxybutyl Ester

HRID 2167345Notes

Reaction equation

HRID 2167345 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][C@@H:10]([OH:14])[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N+:50]([O:53][CH2:54][CH2:55][CH2:56][CH2:57]O)([O-:52])=[O:51]>C(Cl)Cl>[N+:50]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][O:12][C:11](=[O:13])[C@H:10]([OH:14])[CH2:9][C@H:8]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:6][CH:5]=1)([O-:52])=[O:51]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 100119444-(Nitrooxy)butan-1-olHCID 67969342(2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic acid

Product 1

HCID 86703817(2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic Acid 4-nitrooxybutyl EsterYield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic acid (30 mg, 78 μmol), HOBt (63 mg, 470 μmol), and EDCI (83 μL, 470 μmol) were dissolved into DCM. After stirring for 10 minutes, 4-nitrooxybutan-1-ol (84.1 mg, 623 μmol) was added. The resulting mixture was stirred at room temperature and the reaction monitored for completion (˜30 minutes). The mixture was stirred for an additional 2 hours and then left open to dry. The product was then purified (Interchim reverse phase chromatography column; 35-95% MeCN in water with 0.05% TFA) to yield the title compound (18 mg).

Workup

  1. stirringThe resulting mixture was stirred at room temperature
  2. custommonitored for completion (˜30 minutes)
  3. stirringThe mixture was stirred for an additional 2 hours
  4. waitleft open
  5. customto dry
  6. customThe product was then purified (Interchim reverse phase chromatography column; 35-95% MeCN in water with 0.05% TFA)

Sources & evidence

ORD record
ord-a3877d6a3b5f482bbdb2640bc72731fa
Source dataset
uspto-grants-2015_06
Patent number
US09045443B2

Reaction notes

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