N-(tert-butoxycarbonyl)glycine → HCID 47451721, compound

HRID 1782190Notes

Reaction equation

HRID 1782190 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].[C:10]([NH:17][CH2:18][C:19](O)=[O:20])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][C:19](=[O:20])[CH2:18][NH:17][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH:7]=[CH:8][CH:9]=1)#[CH:2]

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 2724699PyBOP

Product 1

HCID 47451721HCID 47451721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Ethynylaniline (1.0 g, 8.54 mmol), N-Boc glycine (2.7 g, 15.41 mmol) and PyBOP (8.1 g, 15.41 mmol) were combined in dichloromethane (25 mL). Diisopropylethylamine (3.3 g, 25.61 mmol) was added to the solution and the mixture was allowed to stir at room temperature under argon for 10 h. The reaction mixture was diluted with dichloromethane and then washed successively with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography, on silica gel, eluting with 95:5 hexanes:ethyl acetate to yield tert-butyl 2-(3-ethynylphenylamino)-2-oxoethylcarbamate. 1H NMR (CDCl3): 8.45 (br s, 1H), 7.62 (m, 1H), 7.58 (m, 1H), 7.30 (m, 2H), 5.38 (br s, 1H), 3.95 (d, 2H), 3.08 (s, 1H), 1.48 ppm (s, 9H).

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash column chromatography, on silica gel
  6. washeluting with 95:5 hexanes

Sources & evidence

ORD record
ord-e0edcbd0b3fc40dfa3369abff8964eed
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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