Acetic Acid → HCID 131711966, compound

HRID 1732548Notes

Reaction equation

HRID 1732548 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4].[NH:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:10]([C:19](ON1C(=O)CCC1=O)=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.CCN(CC)CC.C(O)(=O)C>CN(C=O)C>[NH:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:10]([C:19]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4])=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 69435D-ThreonineHCID 12790906HCID 12790906, compound

Product 1

HCID 131711966HCID 131711966, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

D-Threonine (4.58 g, 38.5 mmol) was dissolved in 19 ml of 40% Triton B and evaporated to an oil. It was re-evaporated twice from DMF, and the salt obtained was stirred with Boc-Tyr-OSu (13.24 g, 35 mmol) in DMF (80 ml) at 0° C. for 1.5 hr and at 25° C. for 30 hr. A constant pH of 8 was maintained by dropwise addition of Et3N during reaction time. The reaction was acidified to pH 4 with acetic acid. The solvent was evaporated to a syrup, dissolved in chloroform, washed with 0.5 N H2SO4 and water, dried (Na2SO4) and evaporated to low volume. The product was obtained as an amorphous solid from petroleum ether: 9.17 g (68.5%): [α]D25 -42.9° (c 1.4, DMF).

Workup

  1. customevaporated to an oil
  2. customIt was re-evaporated twice from DMF
  3. customthe salt obtained
  4. customThe solvent was evaporated to a syrup
  5. dissolutiondissolved in chloroform
  6. washwashed with 0.5 N H2SO4 and water
  7. dry with materialdried (Na2SO4)
  8. customevaporated to low volume
  9. customThe product was obtained as an amorphous solid from petroleum ether

Sources & evidence

ORD record
ord-73374b92c7ac4170810c7950f68da048
Source dataset
uspto-grants-1980_12
Patent number
US04238390

Reaction notes

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