Sodium Carbonate → HCID 56961221, compound

HRID 870300Notes

Reaction equation

HRID 870300 reaction equation
CS([O:5][C@@:6]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[NH2:23])([C:11]#[C:12][CH:13]1[CH2:15][CH2:14]1)[C:7]([F:10])([F:9])[F:8])(=O)=O.[OH-].[Na+].[C:26]([O-])([O-])=[O:27].[Na+].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>>[CH:13]1([C:12]#[C:11][C@:6]2([C:7]([F:10])([F:9])[F:8])[C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[NH:23][C:26](=[O:27])[O:5]2)[CH2:15][CH2:14]1

Participants

5

Reactant 4

HCID 10340Sodium Carbonate2×HCID 14798Sodium HydroxideHCID 94429TriphosgeneHCID 87279954HCID 87279954, compound

Product 1

HCID 56961221HCID 56961221, compound

Conditions

Temperature
15 °C

Procedure

(R)-2-(2-Amino-5-fluorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol methanesulfonate (CN46619-MSA) of example 4 (14.0 g, 33.5 mmol) in ethyl acetate/heptanes (40 g, 6/4 v/v) was charged to a jacketed 150 mL-reactor with agitator and off-gas scrubber with caustic soda. After addition of aqueous Na2CO3 (12%-w/w, 26.9 g, 30.3 mmol) the mixture was stirred for 5 min at 15° C. The aqueous phase was separated and discarded. Aqueous Na2CO3 (12%-w/w, 34.1 g, 38.4 mmol) was charged to the organic phase, then triphosgene (3.73 g, 12.6 mmol) was added in portions over a period of 25 min at 10° C. The reaction mixture was stirred for 2 h at 8° C.

Workup

  1. customThe aqueous phase was separated
  2. stirringThe reaction mixture was stirred for 2 h at 8° C.

Sources & evidence

ORD record
ord-1ff120da8cb14d9ba588d2821e4457b0
Source dataset
uspto-grants-2015_03
Patent number
US08969550B2

Reaction notes

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