Hydrochloric Acid → HCID 9874986, compound

HRID 1384452Notes

Reaction equation

HRID 1384452 reaction equation
C1C(=O)N([O:8][C:9]([O:11][CH2:12][CH:13]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)=O)C(=O)C1.[NH2:26][C@@H:27]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]([C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C:28]([OH:30])=[O:29].C([O-])([O-])=O.[Na+].[Na+].Cl>CN(C=O)C>[CH2:44]([O:43][C:41]([NH:40][CH2:39][CH2:38][CH2:37][CH2:36][N:35]([C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])[CH2:34][CH2:33][CH2:32][CH2:31][C@H:27]([NH:26][C:9]([O:11][CH2:12][CH:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:20]2[C:25]1=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:8])[C:28]([OH:30])=[O:29])=[O:42])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 10791078HCID 10791078, compound

Product 1

HCID 9874986HCID 9874986, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9-fluorenylmethyl N-succinimidyl carbonate (143 mg, 0.42 mmol) in DMF (1.60 mL) was added to a solution of 9 (135 mg, 0.278 mmol) in 9% Na2CO3 (655.9 mg, 0.557 mmol) at 0° C. and stirred at room temperature for 21 hours under argon. The pH was adjusted to 7.0 with 0.1 N HCl. The mixture was concentrated to an oil and purified by flash chromatography (CHCl3, then 95% CHCl3MeOH) to give 10 (115 mg, 58%) as a colorless oil: 1H NMR (19.2° C.) δ1.22-1.92 (m, 10 H), 3.08 (m, 2 H), 3.16-3.30 (m, 4 H), 4.12 (m, 1 H), 4.21 (t, 1 H, J=6.9), 4.30-4.45 (m, 2 H), 5.04(s, 2H), 5.08 (s, 2 H), 7.22-7.42 (m, 14 H), 7.66 (m, 2 H), 7.78 (d, 2 H, J=7.5); HRMS m/z calcd for C41H46N3O8 708.3285, found 708.3284. [δ]22D=+9.3°(c 1.00, CHCl3).

Workup

  1. concentrationThe mixture was concentrated to an oil
  2. custompurified by flash chromatography (CHCl3

Sources & evidence

ORD record
ord-3ae2c74474c041fb9d6e191a54ff91fd
Source dataset
uspto-grants-2001_07
Patent number
US06258931B1

Reaction notes

Loading…