Ammonia → HCID 54577095, compound

HRID 1261628Notes

Reaction equation

HRID 1261628 reaction equation
C(O)(=O)/C=C\C(O)=O.[C:9]1([C@H:15]([NH:17][C@H:18]([CH2:27][C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=2[F:36])[CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.S(=O)(=O)(O)O.[OH-].[Na+].N>O>[C:9]1([C@H:15]([NH:17][C@H:18]([CH2:27][C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=2[F:36])[CH2:19][C:20]([OH:22])=[O:21])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 86676836HCID 86676836, compound

Product 1

HCID 54577095HCID 54577095, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl (3R)-3-[[(1R)-1-phenylethyl]amino]-4-(2,4,5-trifluorophenyl)-butanoate maleate salt [C] (50 g) was stirred in a mixture of water (250 ml) and conc. sulfuric acid (16 ml) at 70° C. for 2 hours. The pH was adjusted to 4.2±0.2 with aqueous sodium hydroxide solution and then to 7.0±0.2 with ammonia solution. Filtered the solid and purified by suspending in water at 25±5° C. for 1 hr. Filtered and dried to yield 31.3 g (94.5% theoretical yield) of titled product [D], m.p. 144° C., purity by HPLC: 98.8%.

Workup

  1. filtrationFiltered the solid
  2. custompurified
  3. filtrationFiltered
  4. customdried
  5. customto yield

Sources & evidence

ORD record
ord-05156a5f56874b7ea2a455be47413aff
Source dataset
uspto-grants-2013_06
Patent number
US08471016B2

Reaction notes

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