tert-Butanol → Benzyl {3-[({5-[(tert-butoxycarbonyl)amino]pyridin-2-yl}carbonyl)(methyl)amino]propyl}methylcarbamate

HRID 446507Notes

Reaction equation

HRID 446507 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:28])[CH2:12][CH2:13][CH2:14][N:15]([CH3:27])[C:16]([C:18]1[N:23]=[CH:22][C:21](C(O)=O)=[CH:20][CH:19]=1)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:31]([CH2:34]C)CC)C.[N-]=[N+]=[N-].C1([O:45]P([O-])(OC2C=CC=CC=2)=O)C=CC=CC=1.[C:56]([OH:60])([CH3:59])([CH3:58])[CH3:57]>>[C:56]([O:60][C:34]([NH:31][C:21]1[CH:20]=[CH:19][C:18]([C:16]([N:15]([CH3:27])[CH2:14][CH2:13][CH2:12][N:11]([CH3:28])[C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:17])=[N:23][CH:22]=1)=[O:45])([CH3:59])([CH3:58])[CH3:57]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 21964642Diphenylphosphate azideHCID 666715476-[(3-{[(Benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylic acid

Product 1

HCID 66671652Benzyl {3-[({5-[(tert-butoxycarbonyl)amino]pyridin-2-yl}carbonyl)(methyl)amino]propyl}methylcarbamateYield 64%

Procedure

The compound (449 mg, 1.16 mmol) obtained in Example 5b was dissolved in tert-butanol (6 mL), triethylamine (1.78 mL, 1.28 mmol) and diphenylphosphate azide (0.251 mL, 1.16 mmol) were added, and the mixture was stirred with heating to reflux for 3 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v) to give the title compound (339 mg; yield, 64%) as a colorless oily substance.

Workup

  1. temperaturewith heating
  2. temperatureto reflux for 3 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v)

Sources & evidence

ORD record
ord-1dcf2f0017974b1b8cfd47872842f1cf
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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