Methanol → HCID 59137224, compound

HRID 1822470Notes

Reaction equation

HRID 1822470 reaction equation
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][N:15]2[C:38](=[O:49])[NH:39][C@H:40]([CH2:45][N:46]=[N+]=[N-])[CH2:41][CH:42]([CH3:44])[CH3:43])=[O:13])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>C1COCC1>[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][N:15]2[C:38](=[O:49])[NH:39][C@H:40]([CH2:45][NH2:46])[CH2:41][CH:42]([CH3:44])[CH3:43])=[O:13])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 57892975HCID 57892975, compound

Product 1

HCID 59137224HCID 59137224, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 108 (717 mg, 1.07 mmol) in THF (25 ml) was shaken together with PS-triphenylphosphine resin (diphenylphosphino polystyrene) (3.24 g, 1.65 mmol PPh3/g) and methanol (2.5 ml) for 78 hrs. The mixture was filtered and the polymer was washed repeatedly with DCM and methanol. The combined filtrates were evaporated to yield the title compound as a light beige solid foam (685 mg, 99%) with more than 95% purity as determined by reversed phase HPLC. M+H+644.1.

Workup

  1. filtrationThe mixture was filtered
  2. washthe polymer was washed repeatedly with DCM and methanol
  3. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-4b201766edad4c2eb139aeb9652d2e48
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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