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3-(N-methylsulfonyl-N-tert-butoxycarbonylamino)-4-benzyloxy-1-(2,3-epoxypropoxy)-benzene → 1-(3-Methylsulfonylamino-4-benzyloxyphenoxy)-3-(7-piperidinocarbonylmethoxy-tetralin-2-yl-amino)-2-propanol

HRID 1796417
Notes
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Reaction equation

HRID 1796417 reaction equation
[CH3:1][S:2]([N:5]([C:13]1[CH:14]=[C:15]([O:27][CH2:28][CH:29]2[O:31][CH2:30]2)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)C(OC(C)(C)C)=O)(=[O:4])=[O:3].[NH2:32][CH:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][C:37]([O:43][CH2:44][C:45]([N:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)=[O:46])=[CH:38][CH:39]=2)[CH2:34]1>C(O)C>[CH3:1][S:2]([NH:5][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:27][CH2:28][CH:29]([OH:31])[CH2:30][NH:32][CH:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][C:37]([O:43][CH2:44][C:45]([N:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)=[O:46])=[CH:38][CH:39]=2)[CH2:34]1)(=[O:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 114650773-(N-methylsulfonyl-N-tert-butoxycarbonylamino)-4-benzyloxy-1-(2,3-epoxypropoxy)-benzeneHCID 155116422-Amino-7-piperidinocarbonylmethoxy-tetralin

Product 1

HCID 221820811-(3-Methylsulfonylamino-4-benzyloxyphenoxy)-3-(7-piperidinocarbonylmethoxy-tetralin-2-yl-amino)-2-propanolYield 39.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.34 g (0.0052 mole) of 3-(N-methylsulfonyl-N-tert-butoxycarbonylamino)-4-benzyloxy-1-(2,3-epoxypropoxy)-benzene, 71 ml of ethanol and 1.44 g (0.0052 mole) of 2-amino-7-piperidinocarbonylmethoxy-tetralin from preparation 1 (base, racemate) were heated under reflux for 8 hours. It was stirred at ambient temperature overnight and then it was heated again under reflux for a further 6 hours. The solvent was evaporated off, the residue was taken up in 40 ml of ethyl acetate and 32.1 ml of a 3N solution of hydrochloric acid in ethyl acetate were added. It was heated under reflux for 5 hours and evaporated under reduced pressure. It was taken up in water, NH4OH was added until the pH was basic, and it was extracted with ethyl acetate. It was dried, the solvent was evaporated off and the product was purified by silica gel column flash chromatography, eluting with a 9:1 methylene chloride/methanol mixture. 1.3 g of the product of the heading was obtained.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 8 hours
  3. temperatureit was heated again
  4. temperatureunder reflux for a further 6 hours
  5. customThe solvent was evaporated off
  6. addition32.1 ml of a 3N solution of hydrochloric acid in ethyl acetate were added
  7. temperatureIt was heated
  8. temperatureunder reflux for 5 hours
  9. customevaporated under reduced pressure
  10. additionNH4OH was added until the pH
  11. extractionit was extracted with ethyl acetate
  12. customIt was dried
  13. customthe solvent was evaporated off
  14. customthe product was purified by silica gel column flash chromatography
  15. washeluting with a 9:1 methylene chloride/methanol mixture

Sources & evidence

ORD record
ord-a0c38d44d04e42ae816b498f7cf4c7ea
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07030160B2

Reaction notes

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