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N-BOC-ethylenediamine → Ethyl 2-[2-(tert-butoxycarbonylamino)ethylamino]-5-methylamino-thiazole-4-carboxylate

HRID 631826
Notes
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Reaction equation

HRID 631826 reaction equation
Br[C:2]1[S:3][C:4]([NH:12][CH3:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[NH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].CCOP(O)N(C(C)C)C(C)C>O1CCOCC1>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][NH:14][C:2]1[S:3][C:4]([NH:12][CH3:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1)=[O:24])([CH3:23])([CH3:22])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 1954513'-O-ethyl-N,N-diisopropylphosphoramiditeHCID 53613688Ethyl 2-bromo-5-(methylamino)-1,3-thiazole-4-carboxylate

Product 1

HCID 89825793Ethyl 2-[2-(tert-butoxycarbonylamino)ethylamino]-5-methylamino-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-Dioxane
Solvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-bromo-5-methylamino-thiazole-4-carboxylate (546 mg, 2.059 mmol) and tert-butyl N-(2-aminoethyl)carbamate (1.3 g, 8.11 mmol) were combined in anhydrous 1,4-dioxane (15 ml). EDIPA (3 ml, 17.2 mmol) was added and the mixture was heated in a sealed tube for 23 hours at 100° C. The mixture was cooled to room temperature and partitioned between DCM and a saturated solution of sodium bicarbonate. Layers were separated, the aqueous phase was extracted twice with DCM and the combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica, gradient of 30 to 100% ethyl acetate in heptane) to yield 185 mg (0.537 mmol, 26%) MS(ESI) m/z=345.2 [M+1]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between DCM
  3. customLayers were separated
  4. extractionthe aqueous phase was extracted twice with DCM
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography (silica, gradient of 30 to 100% ethyl acetate in heptane)
  8. customto yield 185 mg (0.537 mmol, 26%) MS(ESI) m/z=345.2 [M+1]+

Sources & evidence

ORD record
ord-6c7966313d6e483986bb44f2c77ff9be
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321724B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes