HCID 57989169, compound → HCID 57989183, compound

HRID 471269Notes

Reaction equation

HRID 471269 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-d670f4eb353241ee895fc8d8b525c610
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

Loading…