Tetrahydrofuran → HCID 68090528, compound

HRID 554880Notes

Reaction equation

HRID 554880 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][C@@H:21]([CH3:24])[CH2:22]O.C1(P([C:38]2[CH:43]=[CH:42]C=CC=2)C2C=CC=CN=2)C=CC=CC=1.N(C(OCC)=O)=N[C:46]([O:48]CC)=[O:47].O1CCC[CH2:57]1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:22][C@@H:21]([NH:20][C:46]([O:48][C:43]([CH3:42])([CH3:38])[CH3:57])=[O:47])[CH3:24])[C:9]1[S:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 80307L-AlaninolHCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 6218932-Pyridyldiphenylphosphine2×HCID 53404548Ethyl 2-[(tert-butoxycarbonyl)amino]-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 68090528HCID 68090528, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 2-(tert-butoxycarbonylamino)-4-methylthiazole-5-carboxylate (0.29 g, 1.00 mmol), (S)-(+)-2-amino-1-propanol (0.18 g, 1.00 mmol) and diphenyl-2-pyridinylphosphine (0.40 g, 1.50 mmol) in anhydrous tetrahydrofuran (20.0 mL) was added diethyl azodicarboxylate (0.26 g, 1.50 mmol) at 0° C. The resulting solution was stirred at ambient temperature for 0.5 h. Additional diphenyl-2-pyridinylphosphine (0.13 g, 0.50 mmol) and diethyl azodicarboxylate (0.096 g, 0.50 mmol) were added to the reaction mixture and stirred at ambient temperature for 4 h. The reaction mixture was diluted with ethyl acetate (80 mL) and washed with 25% aqueous ammonium chloride solution (3×20 mL). The organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluted with 15-45% ethyl acetate in hexanes to afford the title compound as a colorless oil (0.35 g, 78%): 1H NMR (300 MHz, CDCl3) δ 5.30 (s, 1H), 4.26 (q, J=7.1 Hz, 2H), 4.18-3.95 (m, 3H), 2.59 (s, 3H), 1.58 (s, 9H), 1.33-1.28 (m, 12H), 1.17 (d, J=6.3 Hz, 3H); MS (ES+) m/z 244 (M−2Boc+1).

Workup

  1. stirringstirred at ambient temperature for 4 h
  2. washwashed with 25% aqueous ammonium chloride solution (3×20 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography
  7. washeluted with 15-45% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a2ad5e3539f3460ab6f554f2ff50a676
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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