Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 68817291, compound

HRID 736820Notes

Reaction equation

HRID 736820 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]2[CH2:23][CH2:22][CH2:21][C@:20]2([CH3:27])[C:24]([OH:26])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(ON)(C)(C)C>C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[C:24](=[O:26])[C@:20]3([CH3:27])[C@H:19]2[CH2:23][CH2:22][CH2:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2777907O-tert-butylhydroxylamineHCID 68818513HCID 68818513, compound

Product 1

HCID 68817291HCID 68817291, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

According to the procedure of Example 53, Step 5, using (1S,2R)-2-({[4-(benzyloxy)phenyl]sulfonyl}amino)-1-methylcyclopentanecarboxylic acid (677 mg, 1.74 mmol), BOP (424 mg, 2.09 mmol), O-tert-butylhydroxylamine (480 mg, 3.82 mmol), and triethylamine (1.2 mL), (1S,5R)-6-{[4-(benzyloxy)phenyl]sulfonyl}-1-methyl -6-azabicyclo[3.2.0]heptan-7-one was obtained (480 mg, 1.29 mmol, 74%) as a colorless solid after purification via column chromatography on silica gel, eluting with 25% ethyl acetate/hexanes. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.19-1.28 (m, 1H) 1.30-1.41 (m, 4H) 1.47-1.58 (m, 2H) 1.75 (dt, J=12.69, 6.41 Hz, 1H) 2.02-2.11 (m, 1H) 2.21 (dd, J=14.15, 5.31 Hz, 1H) 4.10 (d, J=4.04 Hz, 1H) 5.11-5.16 (m, 2H) 7.04-7.10 (m, 2H) 7.35-7.44 (m, 5H) 7.92-7.97 (m, 2H).

Sources & evidence

ORD record
ord-7e2f9f13b1e74f5389eafbda02a8c994
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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