Hydrochloric Acid → HCID 66813710, compound

HRID 1097340Notes

Reaction equation

HRID 1097340 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][C@H:10]([NH:12][C:13]1[C:14]2[S:31][C:30](=[O:32])[NH:29][C:15]=2[N:16]=[C:17]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[N:18]=1)[CH3:11].CC([Si](C)(C)[O:38][CH2:39][CH:40]=O)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C1COCC1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:28][C:22]1[C:23]([F:27])=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][S:19][C:17]1[N:18]=[C:13]([NH:12][C@H:10]([CH3:11])[CH2:9][NH:8][CH2:40][CH2:39][OH:38])[C:14]2[S:31][C:30](=[O:32])[NH:29][C:15]=2[N:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66814237HCID 66814237, compound

Product 1

HCID 66813710HCID 66813710, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from example 12 step f) (100 mg) in dry THF (5 ml) was added [[(1,1-dimethylethyl)dimethylsilyl]oxy]-acetaldehyde (49 mg) followed by sodium triacetoxyborohydride (61 mg) and the mixture stirred for 1 hour. The mixture was acidified with concentrated hydrochloric acid, stirred at room temp for 1 hour then evaporated to dryness. The product was purified (HPLC, Novapak® C18 column, 0.1% aqueous TFA:acetonitrile, gradient elution 75:25 to 5:95 over 15 minutes) to afford the title compound (0.021 g).

Workup

  1. stirringstirred at room temp for 1 hour
  2. customthen evaporated to dryness
  3. customThe product was purified
  4. wash(HPLC, Novapak® C18 column, 0.1% aqueous TFA:acetonitrile, gradient elution 75:25 to 5:95 over 15 minutes)

Sources & evidence

ORD record
ord-b081ec32d1154827a22079daa1f596c8
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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