Benzyl Alcohol → 3-Benzyloxycarbonylamino-1-(4-methoxy-benzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic Acid

HRID 1759688Notes

Reaction equation

HRID 1759688 reaction equation
C([O:5][C:6]([CH:8]1[CH:14](C(O)=O)[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])(C)(C)C.C([N:32]([CH2:36]CC)CCC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[CH2:56]([OH:63])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>O1CCOCC1.C(OC(=O)C)C>[CH2:56]([O:63][C:36]([NH:32][CH:14]1[CH2:13][CH:12]=[CH:11][CH2:10][N:9]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)(=[O:20])=[O:19])[CH:8]1[C:6]([OH:5])=[O:7])=[O:46])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 7616TripropylamineHCID 199401P,P-Diphenylphosphinic azideHCID 155505231-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester

Product 1

HCID 155505273-Benzyloxycarbonylamino-1-(4-methoxy-benzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The reaction is performed under an Argon atmosphere. 1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester (300 mg, 0.73 mmol) is dissolved in 4 ml Dioxane (dry). Tripropylamine (TPA) (98 μl, 0.73 mmol) is added and the reaction is stirred for 15 minutes at RT. Diphenyl phosphoryl azide (157 μl, 0.73 mmol) is added and the reaction is gradually heated to 60° C. for 3 h. The reaction is then allowed to cool to room temperature. Benzyl alcohol (235 μl, 2.2 mmol) is added and the reaction solution is heated to 60° C. over night. The reaction solution is diluted with Ethylacetate and washed with 2 M Citric Acid and Water. The organic phase is separated, dried with MgSO4 and filtrated. The solvent is evaporated and the remaining oil is purified by flash-chromatography, Hexane/Ethylacetate (2:1): Cal. 516.6, found (M)+ 517.

Workup

  1. temperaturethe reaction is gradually heated to 60° C. for 3 h
  2. temperatureto cool to room temperature
  3. temperaturethe reaction solution is heated to 60° C. over night
  4. washwashed with 2 M Citric Acid and Water
  5. customThe organic phase is separated
  6. dry with materialdried with MgSO4
  7. filtrationfiltrated
  8. customThe solvent is evaporated
  9. customthe remaining oil is purified by flash-chromatography, Hexane/Ethylacetate (2:1)

Sources & evidence

ORD record
ord-ec5df558923941c5bc928acab580c1b2
Source dataset
uspto-grants-2005_01
Patent number
US06838454B2

Reaction notes

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