Triethylamine → HCID 131722843, compound

HRID 1595140Notes

Reaction equation

HRID 1595140 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([OH:15])=O)[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[Cl:30]C(OCC(C)C)=O.[C:38]1([CH:44]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:45][CH2:46][NH2:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.CN(C=O)C>[NH2:1][C@H:2]([C:13]([NH:47][CH2:46][CH2:45][CH:44]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:15])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.[ClH:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 796983,3-DiphenylpropylamineHCID 1549483L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 131722843HCID 131722843, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.62 g (2 mmol) of Boc-Thr(Bzl)-OH were dissolved in 10 ml DCM, 2 mmol of triethylamine were added and the solution was cooled to 0° C. With stirring, 2 mmol of isobutyl chloroformate were slowly added. The cooling bath was removed, the solution was stirred for 15 minutes and 2.5 mmol of 3,3-diphenylpropylamine in 2 ml of DMF were added and stirred at room temperature for 1 hour. The solution was evaporated, dissolved in ethyl acetate and extracted with 0.5M KHSO4 solution, sat. NaHCO3 solution and brine, dried with MgSO4 and evaporated. The oily product was dissolved in 10 ml of DCM, and 10 ml of a 4M solution of hydrochloric acid in dioxane were added. After 10 minutes the solvents were evaporated, the product hydrochloride was precipitated with diethyl ether, filtered off, washed with diethyl ether and dried in vacuo to give a white solid. MS analysis: (M+H)+: found 403.1, calc. 403.2.

Workup

  1. customThe cooling bath was removed
  2. stirringthe solution was stirred for 15 minutes
  3. stirringstirred at room temperature for 1 hour
  4. customThe solution was evaporated
  5. dissolutiondissolved in ethyl acetate
  6. extractionextracted with 0.5M KHSO4 solution, sat. NaHCO3 solution and brine
  7. dry with materialdried with MgSO4
  8. customevaporated
  9. dissolutionThe oily product was dissolved in 10 ml of DCM
  10. addition10 ml of a 4M solution of hydrochloric acid in dioxane were added
  11. customAfter 10 minutes the solvents were evaporated
  12. customthe product hydrochloride was precipitated with diethyl ether
  13. filtrationfiltered off
  14. washwashed with diethyl ether
  15. customdried in vacuo
  16. customto give a white solid

Sources & evidence

ORD record
ord-dd919d53f1124914af790d5c2798ad91
Source dataset
uspto-grants-2001_09
Patent number
US06287794B1

Reaction notes

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