p-Toluenesulfonic acid → HCID 131732223, compound

HRID 1422520Notes

Reaction equation

HRID 1422520 reaction equation
[NH:1]([C:6]([CH3:8])=[O:7])[CH2:2][C:3]([OH:5])=O.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[NH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[NH:1]([C:6]([CH3:8])=[O:7])[CH2:2][C:3]([NH:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[O:5]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8471Triethylamine2×HCID 10972AcetylglycineHCID 62365Isobutyl chloroformateHCID 1116164Benzyl 3-aminopropanoate

Product 1

HCID 131732223HCID 131732223, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

Ac-Gly-OH a (3.77 g, 32.2 mmol) and triethylamine (6.7 mL, 48.1 mmol) were dissolved in 160 mL THF and cooled to −10° C., and isobutylchloroformate (5.02 g, 38.6 mmol) was added. The mixture was stirred at −10° C. for 1 hr. H-beta-Ala-OBzl.PTSA e (11.26 g, 32.0 mmol) and triethylamine (6.7 mL, 48.1 mmol) was dissolved in 160 mL THF, and added into mix anhydride solution. The reaction mixture was stirred at room temperature overnight. The salt was filtrated off and THF was removed in vacuum. The residue obtained was purified by column chromatography using ethyl acetate and heptane as eluent to obtain 5.95 g Ac-Gly-beta-Ala-OBzl f.

Workup

  1. additionadded
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. filtrationThe salt was filtrated off
  4. customTHF was removed in vacuum
  5. customThe residue obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-dfb1794488f24a57a803b747a2a8d07d
Source dataset
uspto-grants-2015_01
Patent number
US08927499B2

Reaction notes

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