Phenol → Tert-butyl (R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylcarbamate

HRID 1036696Notes

Reaction equation

HRID 1036696 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5]([N:7]1[CH2:24][CH2:23][CH2:22][C@:9]2([C:13](=[O:14])[N:12]([CH3:15])[CH2:11][C@H:10]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8]1)=[O:6].[C:33]1(O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:15][N:12]1[CH2:11][C@@H:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@:9]2([CH2:22][CH2:23][CH2:24][N:7]([C:5](=[O:6])[C@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:3][CH2:2][O:1][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:8]2)[C:13]1=[O:14]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86674099tert-butyl (R)-4-hydroxy-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxobutan-2-ylcarbamate

Product 1

HCID 86674100Tert-butyl (R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyl (R)-4-hydroxy-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxobutan-2-ylcarbamate (111 mg; 0.249 mmol) was solubilised in THF (2.5 ml). Phenol (24 mg; 0.249 mmol) was added followed by triphenylphosphine (98 mg; 0.374 mmol). The solution was cooled to 0° C. and diisopropyl azodicarboxylate (0.073 ml; 0.374 mmol) was added. The reaction mixture was warmed to RT slowly and stirred overnight. The solution was concentrated in vacuo and purified by chromatography on silica eluting with 0-10% MeOH in DCM with ammonia. The compound eluted with triphenylphospine oxide and was used crude in the next step.

Workup

  1. temperatureThe reaction mixture was warmed to RT slowly
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified by chromatography on silica eluting with 0-10% MeOH in DCM with ammonia
  4. washThe compound eluted with triphenylphospine oxide

Sources & evidence

ORD record
ord-1583e359f7194d4f86c26c11106c47ce
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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