Triethylamine → HCID 131720358, compound

HRID 726989Notes

Reaction equation

HRID 726989 reaction equation
F[C:2](F)(F)C(O)=O.[O:8]=[C:9]1[C@@H:15]2[C@@H:11]([CH2:12][CH2:13][NH:14]2)[N:10]1[S:16]([OH:19])(=[O:18])=[O:17].[OH:20][CH:21]1[CH2:26]C(=O)N[C:22]1=O.C([C:32]([NH:34][C@H:35]([C:44]([OH:46])=O)[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)=[O:33])(C)(C)C.[CH2:47]([N:49]([CH2:52][CH3:53])[CH2:50][CH3:51])[CH3:48]>CN(C=O)C>[CH2:47]([N:49]([CH2:52][CH3:53])[CH2:50][CH3:51])[CH3:48].[OH:43][C:40]1[CH:39]=[CH:38][C:37]([CH2:36][C@H:35]([NH:34][C:32](=[O:33])[O:20][C:21]([CH3:26])([CH3:2])[CH3:22])[C:44]([N:14]2[CH2:13][CH2:12][C@@H:11]3[C@H:15]2[C:9](=[O:8])[N:10]3[S:16]([OH:19])(=[O:18])=[O:17])=[O:46])=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67446998HCID 67446998, compoundHCID 70017917HCID 70017917, compound

Product 1

HCID 131720358HCID 131720358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (1S,5R)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulphonic acid trifluoroacetate (360 mg, 1.17 mmol) dissolved in abs. DMF (30 ml) was treated with t-butylcarbonyl-L-tyrosine hydroxysuccinimide (440 mg, 1.16 mmol) and triethylamine (120 mg, 1.2 mmol). After stirring for 4 days the DMF was evaporated. The residue was chromatographed over a polymeric, hydrophobic gel (eluent water, then water:methanol 4:1). The fractions containing the product were combined and lyophilized.

Workup

  1. customwas evaporated
  2. customThe residue was chromatographed over a polymeric, hydrophobic gel (eluent water
  3. additionThe fractions containing the product

Sources & evidence

ORD record
ord-b066faccbe9244bca601afba45a76c26
Source dataset
uspto-grants-1998_01
Patent number
US05712268

Reaction notes

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