Acetic Acid → HCID 22184676, compound

HRID 1795070Notes

Reaction equation

HRID 1795070 reaction equation
[C:1]1([CH2:7][CH:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14](=[O:34])[CH2:15][CH:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH2:18][CH2:17]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C1C=C(C(C)C)C(S([N:50]=[N+:51]=[N-:52])(=O)=O)=C(C(C)C)C=1)C.C(O)(=O)C>C1COCC1.C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14](=[O:34])[CH:15]([N:50]=[N+:51]=[N-:52])[CH:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][Si:24]([CH:25]([CH3:27])[CH3:26])([CH:28]([CH3:30])[CH3:29])[CH:31]([CH3:33])[CH3:32])[CH2:18][CH2:17]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 22184675HCID 22184675, compound

Product 1

HCID 22184676HCID 22184676, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Acyl oxazolidinone (1.28 g, 2.62 mmol) from Step G in 30 mL of THF at −78° C. was treated with 5.8 mL (2.89 mmol) of a 1.5 M solution of potassium hexamethyldisilylamide in toluene followed by 973 mg (3.14 mmol) of trisyl azide in 6 mL of THF and quenched by the addition of 634 mg (10.5 mmol) of acetic acid according to the procedure of D. A. Evans et al., J. Amer. Chem. Soc. 1990, 10, 4011. Purification by Biotage chromatography on silica gel (25% ether/hexane) provided 720 mg (52%) of the title compound. 1H NMR (500 MHz, CDCl3) δ 7.39–7.24 9 (m, 5H), 5.12 (d, 0.3H, J=8.7 Hz), 4.97 (d, 0.7H, J=7.5 Hz), 4.72 (m, 1H), 4.25 (m, 2H), 3.61 (d, 0.6H, J=7 Hz), 3.51 (d, 1.4H, J=5.9 Hz), 3.33 (dd, 1H, J=3 and 4 Hz), 2.87 (dt, 1H, J=3 and 10 Hz), 2.0–1.4 (m, 8H), 1.07–0.9 (m and d, 24H).

Workup

  1. customPurification by Biotage chromatography on silica gel (25% ether/hexane)

Sources & evidence

ORD record
ord-a6fe385fc5974d0f8b2283ec4f4a9e5d
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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