Ammonia → HCID 57989070, compound

HRID 471276Notes

Reaction equation

HRID 471276 reaction equation
N.[OH:2][C@H:3]([C:38]1[C:46]2[S:45][C:44](=[O:47])[NH:43][C:42]=2[C:41]([OH:48])=[CH:40][CH:39]=1)[CH2:4][N:5]([CH2:13][CH2:14][C:15]1[CH:19]=[C:18]([CH2:20][N:21]2[CH2:37][CH2:36][C:24]3([O:29][CH2:28][CH2:27][N:26](C(=O)C(F)(F)F)[CH2:25]3)[CH2:23][CH2:22]2)[S:17][CH:16]=1)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]>>[O:29]1[C:24]2([CH2:23][CH2:22][N:21]([CH2:20][C:18]3[S:17][CH:16]=[C:15]([CH2:14][CH2:13][N:5]([CH2:4][C@H:3]([OH:2])[C:38]4[C:46]5[S:45][C:44](=[O:47])[NH:43][C:42]=5[C:41]([OH:48])=[CH:40][CH:39]=4)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH:19]=3)[CH2:37][CH2:36]2)[CH2:25][NH:26][CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 57989326HCID 57989326, compound

Product 1

HCID 57989070HCID 57989070, compound

Procedure

35% Aqueous ammonia (5 mL) was added to (R)-tert-butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(2-(5-((4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)thiophen-3-yl)ethyl)carbamate (Example 264, step c) (0.2 g). After 40 min at 20° C. the solution was concentrated to ˜1 mL and the slurry added to a C18 (10 g) cartridge washing with water (20 mL), then eluting the product with methanol. The fractions containing product were combined and evaporated in vacuo. The resulting solid was dissolved in acetonitrile and evaporated in vacuo. Yield 0.11 g.

Workup

  1. concentrationAfter 40 min at 20° C. the solution was concentrated to ˜1 mL
  2. additionthe slurry added to a C18 (10 g) cartridge
  3. washwashing with water (20 mL)
  4. washeluting the product with methanol
  5. additionThe fractions containing product
  6. customevaporated in vacuo
  7. dissolutionThe resulting solid was dissolved in acetonitrile
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-8cc5493c3656495aac903d924e4fbfbc
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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