Triethylamine → (S)-tert-Butyl 1-(2-(benzo[d]oxazol-2-ylamino)ethylamino)-1-oxopent-4-yn-2-ylcarbamate

HRID 447146Notes

Reaction equation

HRID 447146 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH2:10][C:11]#[CH:12])=[O:7])([CH3:4])[CH3:3].O.ON1C2C=CC=CC=2N=N1.[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:36][CH2:37][CH2:38][NH2:39].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:36][CH2:37][CH2:38][NH:39][C:13](=[O:15])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:10][C:11]#[CH:12]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734488(2S)-2-{[(tert-butoxy)carbonyl]amino}pent-4-ynoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 61004338N1-(benzo[d]oxazol-2-yl)ethane-1,2-diamine

Product 1

HCID 86654767(S)-tert-Butyl 1-(2-(benzo[d]oxazol-2-ylamino)ethylamino)-1-oxopent-4-yn-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cold mixture of Boc-L-propargyl-glycine (128.2 mg, 0.602 mmol), N-hydroxybenzotriazole hydrate (84.5 mg, 0.625 mmol) and the hydrochloride salt of N1-(benzo[d]oxazol-2-yl)ethane-1,2-diamine (152.3 mg, 0.609 mmol) in dichloromethane (6 mL) was cooled in an ice bath, then treated with triethylamine (0.34 mL, 2.44 mmol) and 1-[3-dimethylaminopropyl]-3-ethyl carbodiimide hydrochloride (119.6 mg, 0.624 mmol). The resulting mixture was stirred for 40 h at room temperature, then diluted with dichloromethane, washed with water, dried over sodium sulfate, filtered and concentrated to yield a residue The residue was purified by flash column chromatography, eluting with 8% methanol in chloroform to yield (S)-tert-butyl 1-(2-(benzo[d]oxazol-2-ylamino)ethylamino)-1-oxopent-4-yn-2-ylcarbamate as a solid.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield a residue The residue
  6. customwas purified by flash column chromatography
  7. washeluting with 8% methanol in chloroform

Sources & evidence

ORD record
ord-0f96a8c2e3fc482291f508d3a4b1762f
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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