L-Serine → FMOC-Ser-Ser-OMe

HRID 353353Notes

Reaction equation

HRID 353353 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[CH:5]([CH2:7][OH:8])[NH2:6].[NH2:10][C@H:11]([C:14]([OH:16])=O)[CH2:12][OH:13].N1[C:22]([CH3:23])=[CH:21][C:20](C)=[CH:19][C:18]=1[CH3:25].CN(C(ON1N=N[C:36]2[CH:37]=[CH:38][CH:39]=N[C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:50][CH2:51][O:52][C:53](C)=[O:54]>CN(C=O)C>[NH:10]([C:53]([O:52][CH2:51][CH:50]1[C:19]2[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:54])[C@H:11]([C:12]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:9])[CH2:7][OH:8])=[O:13])[CH2:14][OH:16]

Participants

7

Reactant 5

HCID 5951L-SerineHCID 79532,4,6-TrimethylpyridineHCID 8857Ethyl AcetateHCID 517373Methyl DL-serinate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 131722996FMOC-Ser-Ser-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of either D, L, or DL serine methyl ester hydrochloride (1.0 eq.) and FMOC-D, L or DL serine (1 eq.) in DMF (0.2 M) is added collidine (3 eq.), followed by HATU (1.1 eq). The resulting solution is stirred at rt overnight, and then diluted with EtOAc and washed with 5% NaHCO3, dried over MgSO4, concentrated in vacuo, and chromatographed on silica gel (EtOAc/hexane) to provide a nearly quantitative yield of FMOC-Ser-Ser-OMe. This material can be prepared as either the DD, DL, LD, or LL stereoisomers, or a mixture of any of the above by varying the chirality of the starting serine derivatives.

Workup

  1. washwashed with 5% NaHCO3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customchromatographed on silica gel (EtOAc/hexane)

Sources & evidence

ORD record
ord-91fb5af721544b32810314e09d39a51c
Source dataset
uspto-grants-2004_06
Patent number
US06750344B1

Reaction notes

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