Triphenylphosphine → tert-butyl ((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate

HRID 2277160Notes

Reaction equation

HRID 2277160 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.O[CH2:24][C@@H:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([O:22][CH2:26][C@@H:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[CH3:24])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 66880968DIAD tolueneHCID 867312122-(3-Chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-ol

Product 1

HCID 86731213tert-butyl ((2S)-1-((2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamateYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-ol (1.00 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (0.832 g) and triphenylphosphine (1.25 g) in THF (10 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 2.50 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (1.09 g). 1H NMR (300 MHz, CDCl3) δ 0.39-0.48 (2H, m), 0.61-0.76 (2H, m), 1.14-1.37 (4H, m), 1.46 (9H, s), 3.90-4.04 (4H, m), 4.03-4.19 (1H, m), 4.77 (1H, brs), 6.95 (1H, dd, J=8.7, 2.3 Hz), 7.01 (1H, d, J=8.7 Hz), 7.10 (1H, d, J=2.3 Hz), 7.60 (1H, d, J=8.7 Hz), 8.04 (1H, dd, J=8.5, 2.1 Hz), 8.22 (1H, d, J=1.9 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3831ce0170214cd6addd28689b7ff5ae
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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