HCID 57989169, compound → HCID 57989183, compound

HRID 1689499Notes

Reaction equation

HRID 1689499 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([CH2:32][N:33]2[CH2:49][CH2:48][C:36]3([O:41][CH2:40][CH2:39][N:38](C(=O)C(F)(F)F)[CH2:37]3)[CH2:35][CH2:34]2)[CH:31]=1)[CH2:5][CH2:6][N:7]([CH2:15][C@H:16]([OH:28])[C:17]1[C:25]2[S:24][C:23](=[O:26])[NH:22][C:21]=2[C:20]([OH:27])=[CH:19][CH:18]=1)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]>N>[O:41]1[C:36]2([CH2:35][CH2:34][N:33]([CH2:32][C:30]3[CH:29]=[C:4]([CH:3]=[C:2]([F:1])[CH:31]=3)[CH2:5][CH2:6][N:7]([CH2:15][C@H:16]([OH:28])[C:17]3[C:25]4[S:24][C:23](=[O:26])[NH:22][C:21]=4[C:20]([OH:27])=[CH:19][CH:18]=3)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:49][CH2:48]2)[CH2:37][NH:38][CH2:39][CH2:40]1

Participants

3

Reactant 1

HCID 57989169HCID 57989169, compound

Product 1

HCID 57989183HCID 57989183, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of (R)-tert-butyl 3-fluoro-5-((4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate (examples 116-182, step a) (0.7 g) in 35% aqueous ammonia solution (15 mL) was allowed to stand at 20° C. for 40 minutes. The reaction mixture was evaporated to half the initial volume under reduced pressure. Water (10 mL) was added and this solution was passed through a 10 g C18 silica cartridge which had been pre-wetted with water. The column was flushed with water (20 mL). The column was then flushed with methanol (50 mL) to bring off the product. The solvent was evaporated under reduced pressure and the residue was azeotroped with acetonitrile (×2) to afford the subtitled compound. Yield 0.580 g.

Workup

  1. customThe reaction mixture was evaporated to half the initial volume under reduced pressure
  2. additionWater (10 mL) was added
  3. customThe column was flushed with water (20 mL)
  4. customThe column was then flushed with methanol (50 mL)
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was azeotroped with acetonitrile (×2)

Sources & evidence

ORD record
ord-38a819c01a814f1ea07451ac9076ea76
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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