Butylamine → HCID 69528746, compound

HRID 1796411Notes

Reaction equation

HRID 1796411 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([OH:23])=O)=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:25]1[C:29](=O)[CH2:28][CH2:27][C:26]1=O.C1(N=C=NC2CCCCC2)CCCCC1.C(N)CCC>C(#N)C.C(OCC)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:23])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8007ButylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 69529788HCID 69529788, compound

Product 1

HCID 69528746HCID 69528746, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

4 g (0.0013 mole) of (2S)-2-tert-butoxycarbonylamino-7-hydroxycarbonylmethoxy-tetralin and 1.66 g (0.0143 mole) of N-hydroxysuccinimide in 40 ml of acetonitrile were stirred at ambient temperature for 3 hours and 2.95 g (0.0143 mole) of DCC (dicyclohexylcarbodiimide) in 15 ml of ethyl ether were added. 1.3 ml (0.0195 mole) of n-butylamine were then added and it was stirred at ambient temperature overnight. The solvent was evaporated off, the residue was taken up in water; it was extracted with ethyl acetate. The organic phase was washed with an aqueous sodium bicarbonate solution, dried and the solvent was evaporated off under reduced pressure. The residue was taken up in a 1:1 ethyl acetate/hexane mixture; the precipitate formed was filtered off and oven dried. The product of the heading was obtained as a white solid.

Workup

  1. customThe solvent was evaporated off
  2. extractionit was extracted with ethyl acetate
  3. washThe organic phase was washed with an aqueous sodium bicarbonate solution
  4. customdried
  5. customthe solvent was evaporated off under reduced pressure
  6. customthe precipitate formed
  7. filtrationwas filtered off
  8. customoven dried
  9. customThe product of the heading was obtained as a white solid

Sources & evidence

ORD record
ord-21e56bcc7ae94d299a07ff44ec7c731b
Source dataset
uspto-grants-2006_04
Patent number
US07030160B2

Reaction notes

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