Triphenylphosphine → methyl 2-((S)-6-((4-(benzyloxy)-2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280686Notes

Reaction equation

HRID 2280686 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([O:22][C@@H:23]3[CH2:27][CH2:26][O:25][CH2:24]3)=[CH:17][C:16]=2[CH3:28])=[CH:11][C:10]=1[CH2:29][OH:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:32]1[CH:45]=[CH:44][C:35]2[C@H:36]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:37][O:38][C:34]=2[CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([O:22][C@@H:23]3[CH2:27][CH2:26][O:25][CH2:24]3)=[CH:17][C:16]=2[CH3:28])=[CH:11][C:10]=1[CH2:29][O:30][C:32]1[CH:45]=[CH:44][C:35]2[C@H:36]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:37][O:38][C:34]=2[CH:33]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 89701807(R)-(4-(benzyloxy)-2',6'-dimethyl-4'-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol

Product 1

HCID 117699398methyl 2-((S)-6-((4-(benzyloxy)-2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetateYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(R)-(4-(Benzyloxy)-2′,6′-dimethyl-4′-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol 36a (637 mg, 1.69 mmol) was dissolved in 20 mL of dichloromethane, followed by addition of methyl (S)-2-(6-hydroxyl-2,3-dihydrobenzofuran-3-yl)acetate (423 mg, 2.03 mmol) and triphenylphosphine (532 mg, 2.03 mmol). The reaction solution was cooled down to 0° C., followed by addition of diisopropyl azodicarboxylate (411 mg, 2.03 mmol), then warmed up to room temperature and stirred for 12 hours. The resulting solution was concentrated under reduced pressure to obtain the crude title compound methyl 2-((S)-6-((4-(benzyloxy)-2′,6′-dimethyl-4′-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 36b (1 g) as a brown oil, which was used directly in the next step without further purification.

Workup

  1. temperaturewarmed up to room temperature
  2. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb972ad66044445c9376fb8c1f043b32
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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