P,P-Diphenylphosphinic azide → HCID 22136236, compound

HRID 1827296Notes

Reaction equation

HRID 1827296 reaction equation
C([CH:8]1[N:12]([CH2:13][C:14]([OH:16])=O)[C:11](=[O:17])[C:10]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(OC(C)(C)C)=O.O.[C:30](=[O:33])([O-:32])[O-].[K+].O.O.[K+].[K+].[K+].[C:40](=O)([O-])[O-].C1(P(N=[N+]=[N-])([C:52]2[CH:57]=[CH:56]C=CC=2)=O)C=CC=CC=1.[N+:61]([CH2:63][C:64]([O:66][CH3:67])=[O:65])#[C-:62]>CN(C=O)C.[Na+].[Cl-]>[C:57]([O:32][C:30]([N:20]1[CH2:19][CH2:18][C:10]2([N:9]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:8][N:12]([CH2:13][C:14]3[O:16][CH:62]=[N:61][C:63]=3[C:64]([O:66][CH3:67])=[O:65])[C:11]2=[O:17])[CH2:22][CH2:21]1)=[O:33])([CH3:56])([CH3:52])[CH3:40]

Participants

7

Reactant 4

HCID 199401P,P-Diphenylphosphinic azideHCID 547815Methyl isocyanoacetateHCID 2734018Potassium carbonate sesquihydrateHCID 70699990HCID 70699990, compound

Product 1

HCID 22136236HCID 22136236, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) mixture of Boc 3-carboxymethyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (3.893 g, 0.010 mol), and potassium carbonate sesquihydrate (6.606 g, 0.040 mol) in DMF (20 mL) was added diphenylphosphoryl azide (3.03 mL, 14.0 mmol) and methyl isocyanoacetate (1.9 mL, 20.9 mmol). The reaction mixture was stirred for 1 day at room temperature. The reaction was then diluted with aq NaCl and extracted with CHCl3 (150 mL). The organic solution was dried over Na2SO4, filtered and concentrated to a brown oil. The crude product was purified by flash chromatography twice (2% MeOH in CHCl3) to yield 3-(4-methoxycarbonyloxazol-5-ylmethyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylic acid-t-butyl ester as a tacky solid.

Workup

  1. extractionextracted with CHCl3 (150 mL)
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to a brown oil
  5. customThe crude product was purified by flash chromatography twice (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-6839ed8fe17e44c98fdd56fccff3388c
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

Loading…