Triphenylphosphine → (S)-4-(4-Benzyl-2H-tetrazol-5-yl)-2-tert-butoxycarbonylamino-butyric acid benzyl ester

HRID 1970511Notes

Reaction equation

HRID 1970511 reaction equation
[CH2:1]([O:8][C:9](=[O:31])[C@@H:10]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:11][CH2:12][C:13](=O)[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C[Si]([N:69]=[N+:70]=[N-:71])(C)C.N([O-])=O.[Na+]>C(#N)C.O>[CH2:1]([O:8][C:9](=[O:31])[C@@H:10]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:11][CH2:12][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:69][NH:70][N:71]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 15674275(S)-4-Benzylcarbamoyl-2-tert-butoxycarbonylamino-butyric acid benzyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 66854446(S)-4-(4-Benzyl-2H-tetrazol-5-yl)-2-tert-butoxycarbonylamino-butyric acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 0.83 g (S)-4-benzylcarbamoyl-2-tert-butoxycarbonylamino-butyric acid benzyl ester and 1.28 g triphenylphosphine in 16 ml acetonitrile were added dropwise at 0° C. 1.00 ml diisopropylazodicarboxylate and after 2 minutes 0.67 ml trimethylsilylazide over a period of 10 minutes. After 30 minutes the mixture was allowed to warm to RT and stirred for 12 h. The mixture was cooled to 0° C. and 0.67 ml aqueous sodium nitrite (2.9 M) were added, after 30 minutes a solution of 1.07 g ceric ammonium nitrate in 10 ml water was added and stirred for another 20 minutes. After this time the mixture was poured into ice and extracted twice with dichloromethane.

Workup

  1. additionwere added dropwise at 0° C
  2. temperatureThe mixture was cooled to 0° C.
  3. additionwas added
  4. stirringstirred for another 20 minutes
  5. additionAfter this time the mixture was poured into ice
  6. extractionextracted twice with dichloromethane

Sources & evidence

ORD record
ord-9576ce0d212f4a8b9a62fec9ac2b9827
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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