Triethylamine → HCID 57517901, compound

HRID 1610995Notes

Reaction equation

HRID 1610995 reaction equation
C(OC([NH:8]CC(O)=O)=O)(C)(C)C.C(N(CC)CC)C.[Cl:20]C(OCC(C)C)=O.[C:28]([NH:31][CH:32]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[Cl:50])[C:37]=1[O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[Cl:59])[C:33]([OH:35])=[O:34])(=[O:30])[CH3:29]>C1COCC1.CCOC(C)=O>[ClH:20].[NH2:8][CH2:29][C:28]([NH:31][CH:32]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[Cl:50])[C:37]=1[O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[Cl:59])[C:33]([OH:35])=[O:34])=[O:30]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 10151939HCID 10151939, compound

Product 1

HCID 57517901HCID 57517901, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-t-butyloxycarbonyl glycine under argon at −5° C. in THF (2 mL) was added triethylamine (60 μL, 0.5 mmol) and then isobutyl chloroformate (67 μL, 0.52 mL). The resulting slurry was stirred 20 min and a solution of Example 13 Part A compound (222 mg, 0.45 mmol) and triethylamine (70 μL, 0.6 mmol) in THF (1 mL) was added over 1 min. The reaction was allowed to warm to room temperature and stirred. After 1 h, the reaction mixture was diluted with EtOAc, washed once with 10% citric acid, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 102 mg (37% yield). LC/MS gave the correct molecular ion [(M+H)+=617] for the desired compound.

Workup

  1. stirringstirred
  2. waitAfter 1 h
  3. washwashed once with 10% citric acid
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9ff32234932f4139b3479147316829f6
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

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