HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Serine → (2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanamide hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Serine | HCID 5951 | — |
| Reactant | 2-Naphthalenesulfonyl chloride | HCID 7125 | — |
| Reactant | (2S)-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanoic acid | HCID 14030411 | — |
| Reactant | 1,1-Dimethylethyl 1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl-carbamate | HCID 22665607 | — |
| Reactant | N-[1-[(1-Amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-yl)sulfonyl]amino]acetamide hydrochloride | HCID 22665631 | — |
| Product | (2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanamide hydrochloride | HCID 69781330 | — |
Reaction Steps
The procedure described for 5c was used. Deprotection of 5a and coupling with (2S)-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanoic acid (prepared from L-serine and 2-naphthalenylsulfonylchloride using the procedure described for 5b) yielded 7. 1H-NMR 200 MHz (CD3OD) δ: 1.12-1.58 (6H, m), 2.57-2.69 (1H, m) 2.95-3.95 (8H, m), 4.9-5.1 (1H, m), 7.11-7.22 (1H, m), 7.43-8.16 (9H, m), 8.24-8.34 (1H, m), 8.41-8.45 (1H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06444672B1 |
| Source dataset | uspto-grants-2002_09 |
| ORD ID | ord-e201258e1fbc4641b735733f177904b0 |
| Source note | uspto-grants-2002_09 |