2-(Tributylstannyl)-1,3-thiazole → HCID 23387580, compound

HRID 990009Notes

Reaction equation

HRID 990009 reaction equation
[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@H:3]1[NH:11][C:12](=[O:48])[C@H:13]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44](Br)=[CH:43][CH:42]=1)[C@H:14]([OH:38])[C@@H:15]([OH:37])[C@@H:16]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=1)[C:17]([NH:19][C@H:20]([C:24](=[O:27])[NH:25][CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:18].C([Sn](CCCC)(CCCC)[C:54]1[S:55][CH:56]=[CH:57][N:58]=1)CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@H:3]1[NH:11][C:12](=[O:48])[C@H:13]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:54]2[S:55][CH:56]=[CH:57][N:58]=2)=[CH:43][CH:42]=1)[C@H:14]([OH:38])[C@@H:15]([OH:37])[C@@H:16]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:54]2[S:55][CH:56]=[CH:57][N:58]=2)=[CH:32][CH:31]=1)[C:17]([NH:19][C@H:20]([C:24](=[O:27])[NH:25][CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:18]

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 23387581HCID 23387581, compound

Product 1

HCID 23387580HCID 23387580, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N1-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-1-indenyl]-N6-[(1S)2-methyl-1-(methylcarbamoyl)propyl]-(2R,3R,4R,5R)-2,5-di(4-bromobenzyloxy)-3,4-dihydroxyhexanediamide, prepared analagously to Example 11 of WO98/45330 using 4-bromobenzyl (130 mg, 0.164 mmol), tributyl-2-thiazolyltin (554 mg, 1.47 mmol), PdCl2(PPh3)2 (120 mg, 0.5 M suspension in DMF), and dry DMF (3 ml) was twice degassed and flushed with argon and then stirred at 90° C./16 h, evaporated to near dryness, washed with a little ether and purified by silica gel column chromatography (chloroform-methanol 20:1) to yield 95.5 mg (73%) of off-white solid.

Workup

  1. customwas twice degassed
  2. customflushed with argon
  3. customevaporated
  4. washwashed with a little ether
  5. custompurified by silica gel column chromatography (chloroform-methanol 20:1)

Sources & evidence

ORD record
ord-23c855c4b2ae4d1684c5a6f4921d46fd
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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