L-Serine → FMOC-Ser-Ser-OMe

HRID 429613Notes

Reaction equation

HRID 429613 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-5424a6f4469f46f28f2b91f86e1bb85f
Source dataset
uspto-grants-2001_11
Patent number
US06316626B1

Reaction notes

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