Dimethylformamide → 4-Amino-L-proline

HRID 851856Notes

Reaction equation

CN([C:4]([O:8]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N([OH:34])N=NC=2C=1.[CH3:35][CH2:36][N:37](C(C)C)C(C)C.C[N:45]([CH:47]=O)[CH3:46]>>[NH2:37][CH:36]1[CH2:47][NH:45][C@H:46]([C:4]([OH:8])=[O:34])[CH2:35]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 757711-Hydroxybenzotriazole

HCID 81531Diisopropylethylamine

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 211203764-Amino-L-proline

Procedure

To the resin was added the corresponding acylating agent (usually a carboxyxlic acid (R64′COOH, 3 equiv.), HBTU (22.3 mg, 4 equiv.), HOBt (8 mg, 4 equiv.) and DIEA (125 μL, 6 equiv.) in DMF (2 mL) for 1.5–2 hrs at room temperature. The resin was filtered, washed with 2×DMF, 3×CH2Cl2, 2×DMF.

Workup

filtrationThe resin was filtered
washwashed with 2×DMF, 3×CH2Cl2, 2×DMF

Sources & evidence

ORD record: ord-ed61f884f7d44b3b8a586e3bda8852f2
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253146B2

Reaction notes

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