p-Toluenesulfonic acid → Ac-Gly-Sar-OBzl

HRID 1422521노트

반응식

HRID 1422521 반응식
[NH:1]([C:6]([CH3:8])=[O:7])[CH2:2][C:3](O)=[O:4].[NH:9]([CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])[CH3:10].[CH3:22][C:23]1[CH:24]=[CH:25][C:26](S(O)(=O)=O)=[CH:27][CH:28]=1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:6]([CH3:8])=[O:7])[CH2:2][C:3]([N:9]([CH2:11][C:12]([O:14][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:13])[CH3:10])=[O:4]

참가 물질

8

반응물 6

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 10972AcetylglycineHCID 757711-HydroxybenzotriazoleHCID 7019103Benzyl 2-(methylamino)acetate

생성물 1

HCID 131732224Ac-Gly-Sar-OBzl

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ac-Gly-OH a (4.10 g, 35.0 mmol), Sar-OBzl.PTSA b (11.71 g, 33.3 mmol), triethylamine (5.58 mL, 40.0 mmol), HOBt (1.35 g, 10 mmol) and DCC (8.25 g, 40.0 mmol) were stirred in 200 mL THF overnight. The mixture was filtered to discard DCU and removed THF in vacuum. The concentrated residue was dissolved in 100 mL ethyl acetate and washed with 100 mL 10% citric acid(aq) twice, 100 mL 5% NaHCO3(aq) twice and 100 mL brine twice, dried over MgSO4, and evaporated in vacuum to get about 9 g light yellow oily Ac-Gly-Sar-OBzl c.

후처리

  1. filtrationThe mixture was filtered
  2. customremoved THF in vacuum
  3. dissolutionThe concentrated residue was dissolved in 100 mL ethyl acetate
  4. washwashed with 100 mL 10% citric acid(aq) twice
  5. dry with material100 mL 5% NaHCO3(aq) twice and 100 mL brine twice, dried over MgSO4
  6. customevaporated in vacuum

출처 및 근거

ORD 기록
ord-9456afc046e5498fa2a63a0f51eb0d90
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927499B2

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