1,2-Dimethoxyethane → HCID 86761253, compound

HRID 250804Notes

Reaction equation

HRID 250804 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[C:35](=[O:41])[C@H:36](CCC)N)C1C=CC=CC=1.C1([N:48]=C=NC2CCCCC2)CCCCC1.CO[CH2:59][CH2:60][O:61]C>>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([CH:36]1[CH2:59][C:60](=[O:61])[NH:48][C:35]1=[O:41])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 86620817L-Norvaline benzyl ester p-toluenesulphonate

Product 1

HCID 86761253HCID 86761253, compound

Procedure

N-Benzyloxycarbonyl-glycine 1 (7.50 g, 35.9 mmol) and N-hydroxysuccinimide 2 (4.13 g, 35.9 mmol) were dissolved in 1,2-dimethoxyethane (60 cm3) and cooled to 0° C. (ice/water) under nitrogen. N,N′-Dicyclohexylcarbodimide (8.14 g, 39.5 mmol) was added and the solution stirred for 1.5 h and then placed in a refrigerator at −5° C. for 20 h. The solution was filtered and evaporated under reduced pressure to form a yellow oil. The oil was triturated with diethyl ether (30 cm3) to form succinimde 3 as a white solid. This solid was used subsequently without further purification.

Workup

  1. waitplaced in a refrigerator at −5° C. for 20 h
  2. filtrationThe solution was filtered
  3. customevaporated under reduced pressure
  4. customto form a yellow oil
  5. customThe oil was triturated with diethyl ether (30 cm3)

Sources & evidence

ORD record
ord-df8dbc15609e465f936a4084405bf93c
Source dataset
uspto-grants-2011_01
Patent number
US07863304B2

Reaction notes

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