Glycinamide hydrochloride → 4-[(4-{3-[(R)-5-Amino-1-(hydroxymethyl)pentylcarbamoyl]propyl}phenyl)methyl]-3-(beta-D-galactopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 2223622Notes

Reaction equation

C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34](/[CH:37]=[CH:38]/[CH2:39][C:40]([OH:42])=O)=[CH:33][CH:32]=2)=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[NH2:46][C@H:47]([CH2:50][CH2:51][CH2:52][CH2:53][NH:54]C(OCC1C=CC=CC=1)=O)[CH2:48][OH:49].Cl.NCC(N)=O>>[NH2:54][CH2:53][CH2:52][CH2:51][CH2:50][C@@H:47]([NH:46][C:40]([CH2:39][CH2:38][CH2:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:43]([CH3:44])[CH3:45])=[CH:36][CH:35]=1)=[O:42])[CH2:48][OH:49]

Participants

Reactant 3

HCID 2723639Glycinamide hydrochloride

HCID 22868988H-D-Lys(Z)-ol

HCID 68537679HCID 68537679, compound

Product 1

HCID 685405064-[(4-{3-[(R)-5-Amino-1-(hydroxymethyl)pentylcarbamoyl]propyl}phenyl)methyl]-3-(beta-D-galactopyranosyloxy)-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 1 using 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazole and (R)-2-amino-6-benzyloxycarbonylamino-1-hexanol instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazole and glycinamide hydrochloride, respectively.

Sources & evidence

ORD record: ord-67eee0508b124646a5691bb284793272
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375087B2

Reaction notes

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