Tetrahydrofuran → HCID 15858322, compound

HRID 1782746Notes

Reaction equation

HRID 1782746 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:41]=[C:42]([Br:45])[C:43]=1[OH:44])[CH2:5][C@H:6]([C:8]([NH:10][C@H:11]([C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:9])[NH2:7].[CH3:46][O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH2:54][NH2:55].[O:56]1CCC[CH2:57]1>>[Br:45][C:42]1[CH:41]=[C:4]([CH:3]=[C:2]([Br:1])[C:43]=1[OH:44])[CH2:5][CH:6]([C:8]([NH:10][C@H:11]([C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:9])[NH:7][C:57]([NH:55][CH2:54][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[O:47][CH3:46])=[O:56]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 812922-MethoxybenzylamineHCID 11527827HCID 11527827, compound

Product 1

HCID 15858322HCID 15858322, compound

Conditions

Temperature
-10 °C

Procedure

A tetrahydrofuran solution (50 ml) of 1.0 g (1.34 mmol) of 1-[N2-(3,5-dibromo-D-tyrosyl)-N6-(phenylmethoxycarbonyl)-L-lysyl]-4-(4-pyridinyl)-piperazine was added dropwise over a period of 40 minutes to a suspension of 0.33 g (2.01 mmol) of CDT in 50 ml of tetrahydrofuran cooled to −10 ° C. and stirred. The reaction mixture was then stirred for 2 hours at ambient temperature and mixed with 0.22 ml (1.675 mmol) of 2-methoxy-benzenemethanamine. Then the mixture was refluxed for 2 hours and stirred overnight at ambient temperature. The reaction mixture was evaporated down in vacuo, the residue was triturated with ether and the solid obtained (1.1 g; 90% of theory) was suction filtered and dried.

Workup

  1. stirringThe reaction mixture was then stirred for 2 hours at ambient temperature
  2. temperatureThen the mixture was refluxed for 2 hours
  3. stirringstirred overnight at ambient temperature
  4. customThe reaction mixture was evaporated down in vacuo
  5. customthe residue was triturated with ether
  6. customthe solid obtained (1.1 g; 90% of theory)
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-502a4dac111a47e0a112588a9c43aa78
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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