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

HRID 2082211

Reaction equation

HRID 2082211 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 131717761Boc-D-Trp(Tos)-OBzlYield 116.1%

Reagents, catalysts & solvents 2

HCID 33992Ethanaminium, N,N,N-trimethyl-, chloride (1:1)CatalystHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-bca4c39040b84e01aa0e7df0d94e2915
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Linked notes

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