Water → [(S)-2-(7-Aminomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

HRID 1453900Notes

Reaction equation

HRID 1453900 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[NH:10][C@@H:11]([CH3:29])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][N:26]=[N+]=[N-])=[CH:22][C:20]3=2)[CH:15]=[N:14]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.O>C1COCC1>[CH2:1]([O:8][C:9](=[O:30])[NH:10][C@@H:11]([CH3:29])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH2:26])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 11776TriphenylphosphineHCID 86612937[(S)-2-(7-Azidomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

Product 1

HCID 68858114[(S)-2-(7-Aminomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Step A (1.28 g, 3.17 mmol) in THF (25 mL) was stirred with polymer supported triphenylphosphine (4 eq, 3 mmol/g, 12.7 mmol, 4.23 g) at 50° C. for 2 hours. Water (2.5 mL) was added and the mixture was stirred for another hour; more water (5 mL) was added and the reaction mixture was filtered. The solids were washed well with THF and the filtrate was evaporated to a residue which was dried under a vacuum to give a foam (1.10 g, 92%): LC/MS m/z 379 [M+H]+.

Workup

  1. customat 50° C.
  2. customfor 2 hours
  3. filtrationthe reaction mixture was filtered
  4. washThe solids were washed well with THF
  5. customthe filtrate was evaporated to a residue which
  6. customwas dried under a vacuum

Sources & evidence

ORD record
ord-b81cadbfcf6c4366b5736bc29f75a63d
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

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