4-Nitrophenyl formate → HCID 131720513, compound

HRID 863243Notes

Reaction equation

[CH2:1]([NH:5][C:6](=[O:35])[C@H:7]([CH3:34])[CH2:8][C@H:9]([OH:33])[C@@H:10]([NH2:32])[CH2:11][C:12]([CH3:31])([CH3:30])[CH2:13][C:14]([N:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:19][CH:18]([C:26]([O:28][CH3:29])=[O:27])[CH2:17]1)=[O:15])[CH2:2][CH2:3][CH3:4].[CH:36](OC1C=CC([N+]([O-])=O)=CC=1)=[O:37]>>[CH2:1]([NH:5][C:6](=[O:35])[C@H:7]([CH3:34])[CH2:8][C@H:9]([OH:33])[C@@H:10]([NH:32][CH:36]=[O:37])[CH2:11][C:12]([CH3:30])([CH3:31])[CH2:13][C:14]([N:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:19][CH:18]([C:26]([O:28][CH3:29])=[O:27])[CH2:17]1)=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 746284-Nitrophenyl formate

HCID 131720510HCID 131720510, compound

Product 1

HCID 131720513HCID 131720513, compound

Procedure

195 mg of 5(S)-amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[2(R,S)-methoxycarbonyl-3,4-dihydro-2H-1,4-benzothiazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide (Example 18)) are reacted with 128 mg of 4-nitrophenyl formate in a manner analogous to that described in Example 17) and the product is purified over 30 g of silica gel (mobile phase M). The title compound is obtained as a yellowish-coloured solid: Rf (N)=0.20; FAB-MS: (M+H)+ =536.

Workup

customis purified over 30 g of silica gel (mobile phase M)

Sources & evidence

ORD record: ord-a0094474144045658ecad9eea724d123
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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