Water → HCID 58052352, compound

HRID 2190206Notes

Reaction equation

HRID 2190206 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:25]([C:26](=[O:29])[NH:27][CH3:28])=[C:24]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)[O:23][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][C@H:18]([CH3:22])[C:19]([OH:21])=[O:20])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.[P:37]([O:55][CH2:56]Cl)([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38].C(#N)C.O>CN(C=O)C>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:25]([C:26](=[O:29])[NH:27][CH3:28])=[C:24]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)[O:23][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][C@H:18]([CH3:22])[C:19]([O:21][CH2:56][O:55][P:37]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])=[O:20])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 11484214Dibenzyl chloromethyl phosphateHCID 58052401HCID 58052401, compound

Product 1

HCID 58052352HCID 58052352, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)-2-methylpentanoic acid (Example 47, 50 mg, 0.090 mmol) and [dibenzyl chloromethyl phosphate (32.5 mg, 0.1 mmol) were stirred in DMF at RT LCMS-80% done at 1 hr Stirred at RT ON-95% done, trace SM and trace mono-de-benzylated side prod.(+) 714 Added 800 μL ACN and 200 μL water Purified on HPLC C18 20-100% ACN/water 1% NH4OH 40 mL/min over 10 min Conc. on vac at 30° C.—no degradation. To give (S)-((bis(benzyloxy)phosphoryl)oxy)methyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-methylpentanoate

Workup

  1. customPurified on HPLC
  2. wait20-100% ACN/water 1% NH4OH 40 mL/min over 10 min Conc. on vac at 30° C.—no degradation

Sources & evidence

ORD record
ord-dbfa3238739c46dba5dd3df9cc3c2bd0
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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