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Methanethiol → (tert-Butoxycarbonylimino-thiomorpholin-4-yl-methyl)-carbamic acid tert-butyl ester

HRID 72804
Notes
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Reaction equation

HRID 72804 reaction equation
[CH3:1][C:2]([CH3:19])([O:4][C:5]([NH:7][C:8](=[N:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])SC)=[O:6])[CH3:3].[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1.CCN(CC)CC.CS>CN(C=O)C.CCOC(C)=O.[Hg]Cl>[C:2]([O:4][C:5](=[O:6])[NH:7][C:8](=[N:11][C:12]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:18])[N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1)([CH3:1])([CH3:3])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 878MethanethiolHCID 8471TriethylamineHCID 67164ThiomorpholineHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 67369775(tert-Butoxycarbonylimino-thiomorpholin-4-yl-methyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 24182
Mercurous Chloride
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of [[[(1,1-dimethylethoxy)carbonyl]amino]-(methylthio)methylene]-carbamic acid, 1,1-dimethylethyl ester [CAS 107819-90-9] (21 g, 0.0723 mol) in DMF (450 mL) was treated sequentially with thiomorpholine (7 mL, 0.0723 mol), mercury chloride (19.6 g, 0.0723 mol), and Et3N (30 mL, 0.22 mol) and the reaction mixture was stirred for 18 h. The mixture was diluted with EtOAc and filtered through a pad of diatomaceous earth. The filtrate was concentrated, diluted with water and EtOAc and filtered again through a pad of diatomaceous earth. The filtrate aqueous layer was separated and extracted with EtOAc (2×). The combined organic layers were washed with water, then satd. aq. NaCl, dried, and concentrated. The solid was triturated with 20% Et2O/40-60° C. petrol. The solid was filtered off and was washed with 20% Et2O/40-60° C. petrol followed by 40-60° C. petrol. The solid was dried under vacuum to give 21.2 g (85%) as a white solid. Note: The reaction was performed with a trap for gaseous loss of methanethiol.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with water and EtOAc
  4. filtrationfiltered again through a pad of diatomaceous earth
  5. customThe filtrate aqueous layer was separated
  6. extractionextracted with EtOAc (2×)
  7. washThe combined organic layers were washed with water
  8. dry with materialaq. NaCl, dried
  9. concentrationconcentrated
  10. customThe solid was triturated with 20% Et2O/40-60° C. petrol
  11. filtrationThe solid was filtered off
  12. washwas washed with 20% Et2O/40-60° C. petrol
  13. customfollowed by 40-60° C.
  14. customThe solid was dried under vacuum
  15. customto give 21.2 g (85%) as a white solid

Sources & evidence

ORD record
ord-ecb393ba31374a78a579de07f0e712fd
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829011B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes