Hydrochloric Acid → Boc-D-Trp(Tos)-OBzl

HRID 2082211

Reaktionsgleichung

Reaktionsgleichung von HRID 2082211
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[OH-].[Na+].[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33].Cl>C(Cl)Cl.[Cl-].C([N+](C)(C)C)C>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:32]([C:35]2[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:5]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 10739405Boc-DTrp-OBzl

Produkt 1

HCID 131717761Boc-D-Trp(Tos)-OBzlAusbeute 116,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 33992Ethanaminium, N,N,N-trimethyl-, chloride (1:1)KatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Boc-D-Trp-OBzl (2.0 g) and ethyltrimethylammonium chloride (16.2 mg) were dissolved in methylene chloride (30 ml), and powdered sodium hydroxide (507 mg) was added. To this mixture was added a solution of Tos-Cl (1.45 g) in methylene chloride (5 ml) at room temperature. The reaction mixture was stirred for three and half an hour. After addition of 1N-hydrochloric acid (7.5 ml), the organic layer was separated, washed with sodium chloride solution, dried over magnesium sulfate, and evaporated to give Boc-D-Trp(Tos)-OBzl as an oil (3.23 g).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bca4c39040b84e01aa0e7df0d94e2915
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05187156

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