Oxolane--water (1/1) → HCID 68862199, compound

HRID 1725907Notes

Reaction equation

HRID 1725907 reaction equation
Br[C:2]1[C:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:21])[CH2:5][CH2:6]2.C1[CH2:26][O:25]CC1.[OH2:27]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(N(CC)CC)C>[O:21]=[C:4]1[C:3]2[C:2]([C:26]([OH:25])=[O:27])=[C:10]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 21881883Oxolane--water (1/1)HCID 68866441HCID 68866441, compound

Product 1

HCID 68862199HCID 68862199, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

A solution of Example 129D (0.1112 g, 0.303 mmol) in 4:1 THF/H2O in a Parr bomb was treated with triethylamine (92 μL) and PdCl2(dppf) (24.8 mg). The bomb was charged to 700 psi with CO, stirred for 24 hours at 120° C., and concentrated. The concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. MS (ESI(+)) m/e 332 (M+H)+, 349 (M+NH4)+, 354 (M+Na)+; MS (ESI(−)) m/e 330 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.72 (m, 1H), 7.52 (m, 4H), 7.33 (d, 1H), 7.22 (d, 1H), 2.99 (m, 1H), 2.88 (m, 1H), 2.73 (m, 1H), 2.27 (m, 1H).

Workup

  1. additionThe bomb was charged to 700 psi with CO
  2. concentrationconcentrated
  3. customThe concentrate was purified by C18 reverse-phase

Sources & evidence

ORD record
ord-07da2d9aef10482c8ec401bb15cad5d8
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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