1-Hydroxybenzotriazole → HCID 67089436, compound

HRID 661087Notes

Reaction equation

HRID 661087 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C@@H:11]([OH:13])[CH3:12])=[CH:5][CH:4]=1.[C:16](NCC(O)=O)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].Cl.C(N=C=NC[CH2:35][CH2:36]N(C)C)C.N1([OH:49])C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:19]([O:18][C:16]([CH2:35][C:36]([O:13][C@H:11](/[CH:10]=[CH:9]/[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=1)[CH3:12])=[O:49])=[O:17])([CH3:20])([CH3:21])[CH3:22]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46915337HCID 46915337, compound

Product 1

HCID 67089436HCID 67089436, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S,E)-4-(4-(Trifluoromethyl)phenyl)but-3-en-2-ol (11.2 g, 51.8 mmol) was taken up in 240 mL of DMF. N-Boc glycine (22.7 g, 130 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (29.8 g, 155 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (21.0 g, 155 mmol), and Hunig's base (27.1 mL, 155 mmol) were added. After 12 hours, the solvent was removed under reduced pressure. The residue was taken up in 500 mL of EtOAc and transferred to a separatory funnel. The mixture was washed with 200 mL of 10% aqueous HCl, 200 mL of aqueous NaHCO3, and 200 mL of brine, and then dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (2.5% to 15% EtOAc/hexanes) afforded (S,E)-4-(4-(trifluoromethyl)phenyl)but-3-en-2-yl 2-(tert-butoxycarbonyl)acetate (16.5 g, 85.3% yield) as a thick oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.59-7.52 (m, 2H) 7.47 (d, J=8.22 Hz, 2H) 6.64 (d, J=15.85 Hz, 1H) 6.26 (dd, J=15.94, 6.55 Hz, 1H) 5.60 (dq, J=6.55, 6.29 Hz, 1H) 5.00 (s, 1H) 3.85-4.00 (m, 2H), 1.46-1.43 (m, 12H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customtransferred to a separatory funnel
  3. washThe mixture was washed with 200 mL of 10% aqueous HCl, 200 mL of aqueous NaHCO3, and 200 mL of brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-1c4e4a796bb04e7f84257eb0d708ef06
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

Loading…