Iodoacetamide → (S)-2-((S)-2-(2-iodoacetamido)-3-methylbutanamido)propanoic acid

HRID 594195Notes

Reaction equation

HRID 594195 reaction equation
[NH2:1][C@@H:2]([CH:15]([CH3:17])[CH3:16])[C:3]([NH:5][C@@H:6]([CH3:14])[C:7]([O:9]C(C)(C)C)=[O:8])=[O:4].[I:18][CH2:19][C:20](N)=[O:21].NC1C=CC=CC=1C1C[C@@H]2N(C=1)C(=O)C1C=C(OC)C(OCCCOC3C(OC)=CC4C(=O)N5C=C(C6C=CC(OC)=CC=6)C[C@H]5C(=O)N(COCC[Si](C)(C)C)C=4C=3)=CC=1N(COCC[Si](C)(C)C)C2=O>ClCCl>[I:18][CH2:19][C:20]([NH:1][C@@H:2]([CH:15]([CH3:16])[CH3:17])[C:3]([NH:5][C@@H:6]([CH3:14])[C:7]([OH:9])=[O:8])=[O:4])=[O:21]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 86676192(S)-2-(2-aminophenyl)-7-methoxy-8-(3-(((S)-7-methoxy-2-(4-methoxyphenyl)-5,11-dioxo-10((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)propoxy)-10-((2-(trimethylsilyl)ethoxy)methyl)-pyrrolo[2,1-c][1,4]-benzodiazepine-5,11(10H,11aH)-dioneHCID 86676194tert-butyl (2S)-2-[(2S)-2-amino-3-methylbutanamido]propanoate

Product 1

HCID 86676195(S)-2-((S)-2-(2-iodoacetamido)-3-methylbutanamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the 97 (100 mg, 0.41 mmol) in dichloromethane was added iodoacetamide-NHS ester (103) (115 mg, 0.41 mmol) and the mixture was stirred at an ambient temperature. After 30 min, the mixture was aspirated onto a 1 mm chromototron plate and eluted with ethyl acetate in hexanes (1:1). A single band was collected and the structure was confirmed: 1H-NMR (400 MHz, CDCl3) δ 6.70 (d, J=7.8 Hz, 1H), 6.27 (d, J=7.0 Hz, 1H), 4.45 (m, 1H), 4.26 (dd, J=8.6, 6.3 Hz, 1H), 3.72 (quart, J=11.3 Hz, 2H), 2.13 (sept, J=6.5 Hz, 1H), 1.47 (s, 9H), 1.38 (d, J=7.1 Hz, 3H), 0.99 (m, 6H); MS (ES+) m/z 412.87 [M+H]+.

Workup

  1. washeluted with ethyl acetate in hexanes (1:1)
  2. customA single band was collected

Sources & evidence

ORD record
ord-acf4557a8c8143bdac3c063c2bf87aa2
Source dataset
uspto-grants-2016_01
Patent number
US09242013B2

Reaction notes

Loading…