Hydrochloric Acid → (S,E)-tert-butyl 4-(4-(methylsulfonyl)-2-aminobut-3-en-1-yl)benzylcarbamate

HRID 1253413Notes

Reaction equation

HRID 1253413 reaction equation
[CH3:1][S:2](/[CH:5]=[CH:6]/[C@@H:7]([NH:24]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][CH:10]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O.C(Cl)Cl.Cl>O>[CH3:1][S:2](/[CH:5]=[CH:6]/[C@@H:7]([NH2:24])[CH2:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[CH:11][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21863450Trifluoroacetic acid methylene chlorideHCID 71562243(S,E)-tert-butyl 4-(4-(methylsulfonyl)-2-(tritylamino)but-3-en-1-yl)benzylcarbamate

Product 1

HCID 71562244(S,E)-tert-butyl 4-(4-(methylsulfonyl)-2-aminobut-3-en-1-yl)benzylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trityl protected amine 17 (0.54 g, 0.90 mmol) was treated with 1% v/v TFA/DCM (15 mL) at room temperature. To this yellow solution was added H2O (1 mL) which resulted in a colourless suspension. After stirring the mixture for 30 minutes, 10 mM aq. HCl (20 mL) was added and DCM was removed under reduced pressure. The aqueous layer was extracted with Et2O (3×) and basified with NaHCO3 until pH 9, after which it was extracted with DCM (3×). The latter combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting deprotected amine proved to be pure on LC-MS analysis and was subjected to the next step without further purification.

Workup

  1. customresulted in a colourless suspension
  2. customDCM was removed under reduced pressure
  3. extractionThe aqueous layer was extracted with Et2O (3×)
  4. extractionafter which it was extracted with DCM (3×)
  5. dry with materialThe latter combined organic layers were dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customwas subjected to the next step without further purification

Sources & evidence

ORD record
ord-7162bd3ad69d4fe6aa23a6a99c06240a
Source dataset
uspto-grants-2013_06
Patent number
US08455431B2

Reaction notes

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