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

HRID 1422521ノート

反応式

HRID 1422521 の反応式
[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]

参加物

8

反応物 6

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

生成物 1

HCID 131732224Ac-Gly-Sar-OBzl

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9456afc046e5498fa2a63a0f51eb0d90
出典データセット
uspto-grants-2015_01
特許番号
US08927499B2

反応ノート

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