Water → HCID 86717552, compound

HRID 712099Notes

Reaction equation

HRID 712099 reaction equation
[N:1]([C@@H:4]1[CH2:9][C@@H:8]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:7]([CH2:21][C:22]#[N:23])[CH2:6][CH2:5]1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][C@@H:4]1[CH2:9][C@@H:8]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:7]([CH2:21][C:22]#[N:23])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86717553HCID 86717553, compound

Product 1

HCID 86717552HCID 86717552, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of benzyl [(1R,2R,5S)-5-azido-2-(cyanomethyl)cyclohexyl]carbamate (45 mg, 0.14 mmol) in tetrahydrofuran (1.5 mL) was added water (13 μL, 0.73 mmol) and resin of triphenylphosphine (150 mg, 0.29 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was filtered and dried in vacuo to give 32 mg of crude product. LCMS calculated for C16H22N3O2 (M+H)+: m/z=288.2. Found: 288.0. The crude was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-ac230b81d2e24c5491ba87cdb0f925a2
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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