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Benzyl Alcohol → 3-[2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-2-tert-butoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester

HRID 1809487
Notes
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Reaction equation

HRID 1809487 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@@H:18]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[N:19]2[CH:24]=[CH:23][CH:22]=[C:21](C(O)=O)[C:20]2=[O:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:38]([CH2:41]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:50])C=CC=CC=1.[CH2:60]([OH:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]([N:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:38][C:41]([O:67][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[O:50])[C:20]2=[O:28])[C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])=[CH:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58674953(S)-3-[2-tert-Butoxycarbonyl-2-(3-carboxy-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 667016723-[2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-2-tert-butoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester
Yield 59.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (S)-3-[2-tert-Butoxycarbonyl-2-(3-carboxy-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (1.8 g, 3.7 mmol) in dioxane was added triethylamine (580 mg, 5.9 mmol), diphenylphosphoryl azide 91.5 g, 5.6 mmol) and benzyl alcohol (680 mg, 6.3 mmol) and the mixture refluxed at 100 C for 18 hours. The mixture was concentrated and partitioned between ethylacetate and saturated bicarbonate. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated to afford the crude product, which was purified by flash chromatography (30-70% ethylacetate/petroleum ether) to afford the title compound as a white solid (1.3 g, 59%); 1H NMR (400 MHz, CDCl3) δ 1.48 (9H, s), 1.73 (9H, s), 3.45 (1H, m), 3.65 (1H, m), 5.2-5.25 (2H, m), 5.60 (1H, m), 6.15 (1H, t), 6.85 (1H, m), 7.25-7.55 (9H, m), 7.95 (1H, m), 8.02-8.18 (2H, m);

Workup

  1. temperaturethe mixture refluxed at 100 C for 18 hours
  2. concentrationThe mixture was concentrated
  3. custompartitioned between ethylacetate and saturated bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product, which
  9. customwas purified by flash chromatography (30-70% ethylacetate/petroleum ether)

Sources & evidence

ORD record
ord-24bc448526e944389d0d63787a94d354
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362043B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes