Dicyclohexylcarbodiimide → HCID 15612344, compound

HRID 845329Notes

Reaction equation

HRID 845329 reaction equation
[C:1]([CH2:5][C:6]([OH:8])=O)([CH3:4])([CH3:3])C.O.O[C:11]1SC2C=CC=CC=2N=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:35][C:36]([CH3:58])([CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1)[C:37]([NH:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:38]>C(OCC)(=O)C>[CH3:11][CH:5]([CH:1]([CH3:3])[CH3:4])[C:6]([NH:35][C:36]([CH3:58])([CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1)[C:37]([NH:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:38])=[O:8]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 14057tert-Butylacetic acidHCID 14560809(+/-)-alpha-amino-alpha-methyl-N-(2-phenylethyl)-1H-indole-3-propanamideHCID 178526942Hydroxybenzothiazole hydrate

Product 1

HCID 15612344HCID 15612344, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 0.14 g (1.2 mmol) of tert-butylacetic acid in 5 ml of ethyl acetate was treated with 0.367 g (2.4 mmol) of hydroxybenzothiazole hydrate, and 0.247 g (1.2 mmol) of dicyclohexylcarbodiimide. After stirring at room temperature for one hour, the product of Example 12 (0.321 g, 1 mmol) was added, together with a few additional milliliters of ethyl acetate. This mixture was stirred overnight at room temperature, and the crude product isolated. Following purification by column chromatography on silica gel, there was obtained 0.095 g of (±)-α-[(2,3-dimethyl-1-oxobutyl)-amino ]-α-methyl-N-(2-phenylethyl)-1H-indole-3-propanamide, mp 104°-109° C.

Workup

  1. stirringThis mixture was stirred overnight at room temperature
  2. customthe crude product isolated
  3. custompurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-5f11e31640b6411aa61075715cdf0dea
Source dataset
uspto-grants-1988_07
Patent number
US04757151

Reaction notes

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