Isopropanol → HCID 58207984, compound

HRID 1958491Notes

Reaction equation

HRID 1958491 reaction equation
C([C:8]1[N:9]=[C:10]([NH2:13])[S:11][CH:12]=1)(OC(C)(C)C)=O.C1(P([C:27]2[CH:32]=[CH:31]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:33][CH:34](O)[CH3:35].CC[O:39][C:40](/N=N/C(OCC)=O)=[O:41].[CH2:49]1COCC1>>[CH:34]([N:13]([C:10]1[S:11][CH:12]=[CH:8][N:9]=1)[C:40](=[O:39])[O:41][C:32]([CH3:31])([CH3:27])[CH3:49])([CH3:35])[CH3:33]

Participants

6

Reactant 5

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 223672711519728-58-5

Product 1

HCID 58207984HCID 58207984, compoundYield 90%

Procedure

To a solution of Boc-2-aminothiazole (400 mg, 2 mmol) in THF (8 mL) at 0° C. was added triphenylphosphine (655 mg, 2.5 mmol) and IPA (0.19 mL, 2.5 mmol). DEAD (0.39 mL<2.5 mmol) was added and the reaction was allowed to warm to room temperature. The reaction was stirred for 2 h then stored at −20° C. overnight. The reaction was then concentrated to an oil and purified directly on silica gel (2.5% EtOAc/heptane) to give tert-butyl isopropyl(thiazol-2-yl)carbamate (432 mg, 90% yield).

Workup

  1. waitthen stored at −20° C. overnight
  2. concentrationThe reaction was then concentrated to an oil
  3. custompurified directly on silica gel (2.5% EtOAc/heptane)

Sources & evidence

ORD record
ord-d883bbaeeaba46e7b4643eb172b4bf74
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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