Carbon Dioxide → HCID 90694713, compound

HRID 1824424Notes

Reaction equation

HRID 1824424 reaction equation
C(O[C:5]([NH:7][CH:8]1[CH:12]([O:13][CH2:14][CH3:15])[O:11][C:10](=[O:16])[CH2:9]1)=[O:6])C=C.C(=O)=O.[C:20]1([C:30]([NH:32][CH:33]2[C:40](=[O:41])[N:39]3[CH:42](C(O)=O)[CH2:43][CH2:44][CH:38]3[CH2:37][CH:36]=[CH:35][CH2:34]2)=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][N:21]=1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[CH2:14]([O:13][CH:12]1[CH:8]([NH:7][C:5]([C@H:42]2[N:39]3[C:40](=[O:41])[C@@H:33]([NH:32][C:30]([C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][N:21]=4)=[O:31])[CH2:34][CH:35]=[CH:36][CH2:37][C@@H:38]3[CH2:44][CH2:43]2)=[O:6])[CH2:9][C:10](=[O:16])[O:11]1)[CH3:15]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22149038(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl esterHCID 69584431HCID 69584431, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 90694713HCID 90694713, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-allyloxycarbonyl-4-amino-5-ethoxy-2-oxotetrahydrofuran (1.83 g, 8.0 mmol) in dichloromethane (30 mL) is added N, N-dimethylbarbituric acid (2.98 g, 47.8 mmol) and tetrakispalladium(0)triphenyl phosphine (0.85 g, 1.9 mmol). The resulting mixture immediately produces CO2 and is allowed to stir at room temperature for 15 minutes after gas evolution has ceased. To this mixture is added 6-[(Isoquinoline-1-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid, 14, (1.2 g, 3.15 mmol), hydroxybenztriazole (1.0 g, 18.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (1.4 g, 18.5 mmol). The reaction mixture is allowed to stir for 2 hours at room temperature. The reaction mixture is poured into water and extracted with ethyl acetate. The organic layers are combined and washed with saturated sodium bicarbonate, brine, dried with sodium sulfate and concentrated in vacuo. The residue is purified over silica (ethyl acetate) to afford 1.42 g (89% yield) of the desired product as a yellow foam. 1H NMR (300 MHz, CDCl3): δ 9.50 (m,1H), 9.02 (d, J=7.7 Hz, 1H), 8.50 (d, J=5.4 Hz, 1H), 7.83 (m, 3H), 7.69–7.41 (m, 3H), 5.84 (m, 1H), 5.70 (m, 1H), 5.49 (m, 2H), 4.71 (m, 2H), 4.26 (m, 1H), 3.90 (m, 1H), 3.71 (m, 1H), 3.17–2.95 (m, 2H), 2.80 (m, 1H), 2.51=2.30 (m, 4H), 2.14 (m,1H), 1.90 (m, 2H), 1.31 (t, J=7.0 HZ, 3H). 13C NMR (CDCl3): δ 173.8, 171.9, 171.0, 165.7, 147.8, 140.8, 137.6, 133.4, 132.4, 132.2, 132.0, 130.7, 130.4, 128.8, 127.7, 127.6, 127.2, 126.0, 124.8, 101.6, 66.0, 61.0, 58.9, 50.3, 48.4, 34.9, 33.5, 33.0, 32.6, 36.6, 15.2. ESI MS-507.15 (M+H).

Workup

  1. stirringto stir for 2 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified over silica (ethyl acetate)

Sources & evidence

ORD record
ord-23a30b9395e04ed1af0ac37315bf5be8
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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