Hydrochloric Acid → HCID 10795481, compound

HRID 1068081Notes

Reaction equation

HRID 1068081 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:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[CH2:36][C@H:37]([O:51][CH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][O:53]1)[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][C@@H:37]([O:51][CH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][O:53]1)[CH2:36][N:35]([C:58]([O:60][CH2:61][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)=[O:59])[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 10841069HCID 10841069, compound

Product 1

HCID 10795481HCID 10795481, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9-fluorenylmethyl N-succinimidyl carbonate (203 mg, 0.60 mmol) in DMF (3.0 mL) was added to a solution of 18a (219 mg, 0.37 mmol) in 9% Na2CO3 (803 mg, 0.68 mmol) at 0° C. and stirred overnight at room temperature. 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% CHCl3/MeOH) to give 11a (150 mg, 50%) as a colorless oil: 1H NMR δ 1.15-1.94 (m, 14H), 3.10-3.52 (m, 7H), 3.66-3.98 (m, 2H), 4.05-4.21 (m, 2H), 4.24-4.61 (m, 3H), 5.04 (s, 2H), 5.08 (s, 2H), 7.21-7.40 (m, 14H), 7.65 (dd, 2H, J=6.9, 4.2), 7.77 (d, 2H, J=7.2); 13C NMR δ 21.1, 21.7, 24.1, 26.4, 26.5, 28.2, 28.9, 32.1, 32.5, 32.6, 33.2, 34.3, 38.1, 38.5, 51.9, 52.4, 55.5, 64.1, 65.2, 67.4, 67.9, 68.3, 74.9, 79.5, 100.0, 101.5, 120.9, 126.3, 128.2, 128.80, 128.97, 129.10, 129.20, 129.48, 129.57, 129.62, 138.2, 138.5, 142.6, 145.2, 145.4, 158.1, 158.6, 176.8; HRMS m/z calcd for C46H54N3O10 808.3809, found 808.3833.

Workup

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

Sources & evidence

ORD record
ord-3cc7f5454cea445c9a00cee13b21fedd
Source dataset
uspto-grants-2001_06
Patent number
US06248866B1

Reaction notes

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