HCID 10667010, compound → HCID 10545394, compound

HRID 589526Notes

Reaction equation

HRID 589526 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:24]C=C)[CH2:8][C@@H:9]([N:21]=[N+:22]=[N-:23])[C@H:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:11]=[CH2:12])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[Cl-].[Cl-].[Zn+2]>[C:1]([O:5][C:6]([N:7]1[CH2:24][CH:12]=[CH:11][C@@H:10]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@H:9]([N:21]=[N+:22]=[N-:23])[CH2:8]1)=[O:27])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10667010HCID 10667010, compound

Product 1

HCID 10545394HCID 10545394, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of Mo(CHCMe2Ph)(NAr)(OCMe(CF3)2)2(phen) (8 mg, 9 μmol, 5 mol %) and ZnCl2 (1.2 mg, 9 μmol) in CH2Cl2 (18 mL) was heated for 30 min to 100° C. Subsequently, (2R,3R)-allyl-(2-azido-3-benzyloxy-pent-4-enyl)-carbamic acid tert-butylester (66 mg, 0.177 mmol) was added and the mixture was heated for 30 min under reflux. After removal of the solvent, the residue is purified by means of column chromatography at silica gel (hexane/ethylacetate, 20:1). 1H NMR (300 MHz, CD2Cl2): δ=7.40-7.29 (m, 5H), 5.76 (br s, 2H), 4.67 (d, J=11.5 Hz, 1H), 4.55 (d, J=11.5 Hz, 1H), 427-3.97 (m, 2H), 3.85-3.54 (m, 4H), 1.45 (s, 9H); 13C NMR (75 MHz, CD2Cl2): δ=155.1, 138.3, 131.1, 129.8, 128.7, 128.3, 128.1, 80.5, 79.1, 72.3, 64.0, 48.8, 47.5, 28.4; [α]20D=6−26.3 (2.65, CH2Cl2); IR (film, cm−1): 3065, 3031, 2976, 2927, 2857, 2108, 1699, 1657, 1496, 1456, 1393, 1366, 1248, 1168, 1135, 1095, 737, 698 cm−1; MS (EI) m/z: 344 ([M+], <1), 260 (1), 225 (2), 186 (1), 180 (3), 169 (14), 160 (6), 125 (11), 91 (100), 57 (57); HRMS (ESI) (C18H24N4O3+H) calculated: 345.1927. found: 345.1921; C18H24N4O3 (344.41) calculated: C, 62.77; H, 7.02; N, 16.27. found: C, 62.72; H, 6.94; N, 16.19. The obtained data correspond to those of literature (A. Fürstner, O. R Thiel, J. Org. Chem. 2000, 65, 1738).

Workup

  1. temperaturethe mixture was heated for 30 min
  2. temperatureunder reflux
  3. customAfter removal of the solvent
  4. customthe residue is purified by means of column chromatography at silica gel (hexane/ethylacetate, 20:1)

Sources & evidence

ORD record
ord-e15e2947a0104425ba1c5018d6736a3a
Source dataset
uspto-grants-2016_01
Patent number
US09233362B2

Reaction notes

Loading…