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1-Hydroxybenzotriazole → (4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid

HRID 722733
Notes
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Reaction equation

HRID 722733 reaction equation
C(OC1C(NC([C@H]2N3C(=O)[C@@H](NC(=O)C4C=CC=CC=4)CC=CC[C@H]3CCC2)=O)CC(=O)O1)C.C(OC(=O)NC1CC(=O)OC1OCC)C=C.[C:51]([NH:59][C@@H:60]1[C:67](=[O:68])[N:66]2[C@H:69]([C:73]([OH:75])=[O:74])[CH2:70][CH2:71][CH2:72][C@H:65]2[CH2:64][CH:63]=[CH:62][CH2:61]1)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:51]([NH:59][C@@H:60]1[C:67](=[O:68])[N:66]2[C@H:69]([C:73]([OH:75])=[O:74])[CH2:70][CH2:71][CH2:72][C@@H:65]2[CH2:64][CH:63]=[CH:62][CH2:61]1)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 22149038(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl esterHCID 69659568(4S,7S,11aS)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acidHCID 86590807(4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

Product 1

HCID 69659744
(4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Preparation of (4S,7S,11aR)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide (45) A catalytic amount of Pd(Ph3P)4 (35 mg, 0.03 mmol) is added to a solution of (2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester (69 mg, 0.3 mmol) and N,N-dimethylbarbituric acid (156 mg, 1.0 mmol) in 2 mL CH2Cl2 at room temperature. The solution is stirred at rt for 15 minutes and (4S,7S,11aS)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid, 44, (40 mg, 0.12 mmol) is added as a solution in 1 mL CH2Cl2, followed by 1-hydroxybenzotriazole (41 mg, 0.3 mmol) and 1-(3-dimethyl-aminopropyl)-3-ethyl-carbodiimide hydrochloride (58 mg, 0.3 mmol). The solution is stirred for 4 hours, diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography over silica gel afforded 32 mg of the desired product. 1H NMR (CDCl3) δ 7.88 (m, 2H), 7.72 (m, 1H), 7.51 (m, 3H), 5.75–5.25 (series of m, 4H), 5.02 (d, J=5.8 Hz, 1H), 4.66 (m, 2H), 3.98 (dq, J=9.3, 7.0 Hz, 1H), 3.73 (dq, J=9.3, 7.0 Hz, 1H), 3.24 (m, 1H), 2.96–1.45 (series of m, 11H), 1.37 (t, J=7.0 Hz, 3H); MS 470 (M+H)+.

Workup

  1. stirringThe solution is stirred for 4 hours
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography over silica gel

Sources & evidence

ORD record
ord-da8aca8e73c746f4bc865eb98655fb53
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07138395B2

Reaction notes

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