Hydrochloric Acid → Boc-Pro-Thr(OBzl)-OH

HRID 2107784Notes

Reaction equation

HRID 2107784 reaction equation
[N:1]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5]N1C(=O)CCC1=O)=O.N1(C(OC(C)(C)C)=O)[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25](O)=O.[NH2:38][C@H:39]([C:43]([OH:45])=[O:44])[C@@H](C)O.C([O-])(O)=O.[Na+].Cl.O1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>O>[N:1]1([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([NH:38][C@H:39]([C:43]([OH:45])=[O:44])[C@@H:54]([CH3:53])[O:55][CH2:56][C:57]1[CH:25]=[CH:24][CH:28]=[CH:29][CH:30]=1)=[O:5]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6288L-ThreonineHCID 312751,4-DioxaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 516892Sodium BicarbonateHCID 8538831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) 2-(2,5-dioxo-1-pyrrolidinyl) ester, (2S)-2×

Product 1

HCID 14836683Boc-Pro-Thr(OBzl)-OH

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Boc-Pro-Thr(OBzl)-OH was prepared by coupling Boc-Pro-OSu (the N-hydroxysuccinamide ester of Boc-Pro-OH) to H-Thr (OBzl) - OH. H-Thr (OBzl)-OH.HCL was dissolved in 25 ml of water, NaHCO3 (6.21 g, 73.9 mmoles) and a solution of Boc-Pro-Osu (5.07 g, 16.25 mmoles) in 25 ml of dioxane were added. After stirring 3 hours, the reaction mixture was acidified with hydrochloric acid and the product extracted into ethyl acetate. It was washed with 0.2N HCl prepared in saturated aqueous NaCl, saturated NaCl and dried over anhydrous Na2SO4. Solvent was evaporated to yield 6.24 g (mp 120°-12.5°).

Workup

  1. extractionthe product extracted into ethyl acetate
  2. washIt was washed with 0.2N HCl
  3. customprepared in saturated aqueous NaCl
  4. dry with materialsaturated NaCl and dried over anhydrous Na2SO4
  5. customSolvent was evaporated
  6. customto yield 6.24 g (mp 120°-12.5°)

Sources & evidence

ORD record
ord-a140bd7236e34961af77af8874e44fb7
Source dataset
uspto-grants-1990_06
Patent number
US04935493

Reaction notes

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