Triethylamine → HCID 131719791, compound

HRID 233634Notes

Reaction equation

HRID 233634 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([NH:14][C:15]([CH3:29])([C:26](O)=[O:27])[CH2:16][C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)=[O:13])[CH2:8]2.[OH2:30].OC1S[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2N=1.C([N:43]([CH2:46][CH3:47])CC)C>C(Cl)Cl>[NH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH2:16][C:15]([NH:14][C:12](=[O:13])[O:11][CH:2]2[CH:3]3[CH2:9][CH:7]4[CH2:6][CH:5]([CH2:10][CH:1]2[CH2:8]4)[CH2:4]3)([CH3:29])[C:26](=[O:27])[NH:43][CH2:46][CH:47]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:30][C:10]3[C:1]2=[CH:2][CH:3]=[CH:4][CH:5]=3)=[CH:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophanHCID 178526942Hydroxybenzothiazole hydrate

Product 1

HCID 131719791HCID 131719791, compoundYield 122,091.203%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-adamantyl oxycarbonyl-α-methyl DL tryptophane (0.79 g, 0.002 mmol) in methylene chloride (60 mL) was treated with hydroxybenzothiazole hydrate (0.3 g, 0. 0022 mmol), 1-(2-dimethylamino propyl)-3-ethylcarbodiimide. HCl (0.38 g, 0.002 mmol) and triethyl amine (0.202 g, 0.002 mmol). After stirring at room temperature for 2 hours a solution of 3H-xanthane-9-methenamine (0.495 g, 0.002 mmol) in methylene chloride (10 mL) was added. The reaction mixture was stirred at room temperature overnight. The clear solution was concentrated in vacuo. The resulting oil was taken up in ethyl acetate. The ethyl acetate solution was washed with 1 NHCl, saturated NdHCO3 and brine. The organic phase was dried over MgSO4 and concentrate in vacuo to give a white foam. The product was chromatographed over silica using 50% ethyl acetate; 50% hexane as eluant to give the title compound (0.72 g, 59%).

Workup

  1. additionwas added
  2. concentrationThe clear solution was concentrated in vacuo
  3. washThe ethyl acetate solution was washed with 1 NHCl, saturated NdHCO3 and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrate in vacuo
  6. customto give a white foam
  7. customThe product was chromatographed over silica using 50% ethyl acetate

Sources & evidence

ORD record
ord-a6aeccef69ca4d37bb30dca481580bd5
Source dataset
uspto-grants-1997_01
Patent number
US05593967

Reaction notes

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